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CAS No. : | 1194700-73-6 | MDL No. : | MFCD24729793 |
Formula : | C9H8O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XCLSUJASPNFYRV-UHFFFAOYSA-N |
M.W : | 164.16 | Pubchem ID : | 66643957 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.76 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.34 cm/s |
Log Po/w (iLOGP) : | 1.52 |
Log Po/w (XLOGP3) : | 1.36 |
Log Po/w (WLOGP) : | 1.22 |
Log Po/w (MLOGP) : | 1.25 |
Log Po/w (SILICOS-IT) : | 2.13 |
Consensus Log Po/w : | 1.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.08 |
Solubility : | 1.35 mg/ml ; 0.00823 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.94 |
Solubility : | 1.89 mg/ml ; 0.0115 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.38 |
Solubility : | 0.683 mg/ml ; 0.00416 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.81 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 0C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature <; 10 0C. After stirring the recation mixture for an additional 15 min, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 min. The biphasic mixture was filtered over Solka floe, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-l-oxo- 13-dihydro-isobenzofuran-5-yl ester. 1H NMR (400 MHz, CDCl3 ): delta 7.87 (d, J= 8.4 Hz, IH), 7.47 (d, J- 8.4 Hz, IH), 5.32 (s, 2H), 2.41 (s, 3H) | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Tnethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 minutes, keeping the temperature < 10 C. After stirring the reaction mixture for an additional 15 minutes, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 minutes. The biphasic mixture was filtered over Solka-Flok powdered cellulose, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-l-oxo-l,3-dihydro-isobenzofuran-5-yl ester. 1H NMR (400 MHz, CDC13 ): delta 7.87 (d, J= 8.4 Hz, 1H), 7.47 (d, J= 8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H) | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C, Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 minutes, keeping the temperature < 10 C. After stirring the reaction mixture for an additional 15 minutes, the reaction mixture was quenched with water (200 mL), and then stirred with DARCO KB (activated carbon, 25 g) for 15 minutes. The biphasic mixture was filtered over Solka-Floc, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, and the solid was washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-l-oxo-l,3-dihydro-isobenzofuran-5-yl ester. 'H NMR (400 MHz, CDCI3 ): delta 7.87 (d, J= 8.4 Hz, 1H), 7.47 (d, J= 8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H). |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature < 10 C. After stirring the reaction mixture for an additional 15 min, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 min. The biphasic mixture was filtered over Solka Floe, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product precipitating during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing the title compound. | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran- 1 -one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in a 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 minutes, keeping the temperature < 10 C. After stirring the reaction mixture for an additional 15 minutes, the reaction mixture was quenched with water (200 mL), and then stirred with DARCO KB (activated carbon, 25 g) for 15 minutes. The biphasic mixture was filtered over Solka-Floc, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, and the solid was washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-l-oxo-l,3-dihydro-isobenzofuran-5-yl ester. 1H NMR (400 MHz, CDC13 ): delta 7.87 (d, J= 8.4 Hz, 1H), 7.47 (d, J= 8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H) | |
With triethylamine; In dichloromethane; at 3.8 - 10℃;Inert atmosphere; | Step D:Trifluoromethanesulfonic acid 4-methyl-1-oxo-1 ,3-dihydro-isobenzofuran-5-yl ester; 5-Hydroxy-4-methyl-3H-isobenzofuran-1-one (46.8 g, 285 mmol) was suspended indichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added viaaddition funnel over 50 min, keeping the temperature < 10 C. After stirring the reaction mixturefor an additional 15 min, the reaction mixture was quenched with water (200 mL ), then stirredwith DARCO KB (activated carbon, 25 g) for 15 min. The biphasic mixture was filtered over Solka Floc, washing with additional dichloromethane, and transferred to a separatory funnel,whereupon it was diluted with additional water (300 mL). The layers were separated, and theorganic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethanesolution was dried over sodium sulfate, filtered and evaporated. The solid was adsorbed ontosilica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product precipitating duringconcentration. The suspension was filtered, the solid washed with heptane and dried undervacuum and nitrogen, providing the title compound. | |
With triethylamine; In dichloromethane; for 1.08333h;Inert atmosphere; | -Hydroxy-4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature < 10 C. After stirring the recation mixture for an additional 15 min, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 min. The biphasic mixture was filtered over Solka floe, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-l-oxo-l,3-dihydro- isobenzofuran-5-yl ester. 1H MR (400 MHz, CDC13 ): delta 7.87 (d, J= 8.4 Hz, 1H), 7.47 (d, J = 8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H) | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl- 1-oxo- l,3-dihydro-isobenzofuran-5-yl ester. 1H NMR (400 MHz, CDC13 ): delta 7.87 (d, J= 8.4 Hz, 1H), 7.47 (d, J= 8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H) | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 0.25h;Inert atmosphere; | Step D: Trifluoromethanesulfonic acid 4-methyl-i -oxo- 1 ,3-dihydro-isobenzofuran-5-yl ester 5-Hydroxy-4-methyl-3H-isobenzofuran-1-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stiffer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled inan ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 mm, keeping the temperature < 10 C. After stirring the reaction mixture for an additional 15 mm, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 mm. The biphasic mixture was filtered over SOLKA FLOC, washing with additional dichloromethane, and transfeffed to a separatory funnel,whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product precipitating duringconcentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing the title compound | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-1-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom fiask equipped with oyerhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added viaaddition funnel oyer 50 mm, keeping the temperature < 10 c. After stirring the reaction mixture for an additional 15 mm, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (actiyated carbon, 25 g) for 15 min. The biphasic mixture was filtered oyer SOLKA FLOc, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, andthe organie layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried oyer sodium sulfate, filtered and eyaporated. The solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetatelhexanes. The resulting solution was concentrated under yacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptaneand dried under yacuum and nitrogen, proyiding trifluoromethanesulfonic acid 4-methyl- 1 -oxo1,3-dihydro-isobenzofuran-5-yl ester. lH NMR (400 MHz, cDcl3): 7.87 (d, J= 8.4 Hz,1H), 7.47 (d, J= 8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H) | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | Step D: 4-methyl-i -oxo- 1,3 -dihydroisobenzofuran-5 -yl trifluoromethanesulfonate: 5 -Hydroxy4-methyl-3H-isobenzofuran-1-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C.Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 mm, keeping the temperature < 10 C. After stirring the recation mixture for an additional 15 mm, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 mm. The biphasic mixture was filtered over Solka-Floc, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it wasdiluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing duringconcentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-i -oxo- 1,3 -dihydroisobenzofuran-5-yl ester. ?H NMR (400 MHz, CDC13): oe 7.87 (d, J 8.4 Hz, iH), 7.47 (d, J 8.4 Hz, iH), 5.32 (s, 2H), 2.41 (s, 3H) | |
With triethylamine; In dichloromethane; at 3.8℃; for 0.833333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-i-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was addedvia addition funnel over 50 mm, keeping the temperature < 10 C. After stirring the reaction mixture for an additional 15 mm, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 mm. The biphasic mixture was filtered over SOLKA FLOC , washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers wereseparated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product precipitating during concentration. The suspension was filtered, the solid washed with heptaneand dried under vacuum and nitrogen, providing the title compound. | |
5-Hydroxy~4~ methyl-3H-isobenzofuran- 1 -one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in a 2-L round botto flask equipped with overhead stirrer under nitrogen. Triethyiamine (59.5 mL, 427 mmol) was added and the reaction mixture was cooled in an ice bath to 3.8C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature at; 10C. After stirring the recation mixture for an additional 15 min, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 minutes. The biphasic mixture was filtered over SolkaFioc, washing with additional dichloromethane and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated and the organic layer was washed with water (500 mL) and .10% brine (200 ml..). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27,5 g) and eiuted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifl.uoromethan.esui fonic acid 4-methy I - 1 -oxo- 1 ,3 -dihydro- isobenzofuran-5-yl ester. MR (400 MHz, CDC13): delta 7.87 (d, J = 8.4 Hz, 1H), 7.47 (d, J= 8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H). | ||
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | Step D : 4-methyl- 1 -oxo- 1 ,3 -dihydroisobenzofuran-5 -yl trifluoromethanesulfonate : 5-Hydroxy- 4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature < 10 C. After stirring the recation mixture for an additional 15 min, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 min. The biphasic mixture was filtered over SOLKA FLOC, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methy 1-1 -oxo- 1,3 -dihydroisobenzofuran-5 -yl ester. | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | Step D: 4-methyl-l-oxo-L3-dihvdroisobenzofuran-5-yl trifluoromethanesulfonate: 5-Hydroxy- 4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature < 10 C. After stirring the recation mixture for an additional 15 min, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 min. The biphasic mixture was filtered over SOLKA FLOC, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-l-oxo-l,3-dihydro- isobenzofuran-5-yl ester | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-1-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8 . Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature < 10 . After stirring the reaction mixture for an additional 15 min, the reaction mixture was quenched with water (200 mL) , then stirred withKB (activated carbon, 25 g) for 15 min. The biphasic mixture was filtered over SOLKA-washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL) . The layers were separated, and the organic layer was washed with water (500 mL) and 10brine (200 mL) . The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25 ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-1-oxo-1, 3-dihydro-isobenzofuran-5-yl ester. 1H NMR (400 MHz, CDCl3) : delta 7.87 (d, J 8.4 Hz, 1H) , 7.47 (d, J 8.4 Hz, 1H), 5.32 (s, 2H) , 2.41 (s, 3H) . | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature < 10C. After stirring the recation mixture for an additional 15 min, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 min. The biphasic mixture was filtered over Solka floe, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-l-oxo- l,3-dihydro-isobenzofuran-5-yl ester. 1H NMR (400 MHz, CDC13 ): delta 7.87 (d, J= 8.4 Hz, 1H), 7.47 (d, J= 8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H) | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h; | Step D: 4-methyl-1 -oxo- 1,3 -dihydroisobenzofuran-5 -yl trifluoromethanesulfonate: 5-Hydroxy-4-methyl-3H-isobenzofuran-1-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added, and the reaction mixture was cooled in an ice bath to 3.8C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 mm, keeping the temperature < 10C. After stirring the recation mixturefor an additional 15 mm, the reaction mixture was quenched with water (200 mL), then stirred with DARCO KB (activated carbon, 25 g) for 15 mm. The biphasic mixture was filtered over Solka floc, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethanesolution was dried over sodium sulfate, filtered and evaporated. The solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-1-oxo-1,3-dihydro-isobenzofuran-5-yl ester. ?H NMR (400 MHz, CDC13): oe 7.87 (d, J= 8.4 Hz, 1H), 7.47 (d, J8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H) | |
With triethylamine; In dichloromethane; at 10℃; for 1.08333h;Inert atmosphere; Cooling with ice; | 5-Hydroxy-4-methyl-3H-isobenzothran-i -one (46.8 g,285 mmol) was suspended in dichloromethane (935 mE) ina 2-E roundbottom flask equipped with overhead stirrerunder nitrogen. Triethylamine (59.5 mE, 427 mmol) wasadded, and the reaction mixture was cooled in an ice bath to3.8 C. Trifluoromethanesulfonic anhydride (67.4 mE, 399mmol) was added via addition thnnel over 50 minutes, keeping the temperature <10 C. Afier stirring the reaction mixture for an additional 15 minutes, the reaction mixture was quenched with water (200 mE), and then stirred with DARCO KB (activated carbon, 25 g) for 15 minutes. Thebiphasic mixture was filtered over Solka-Floc, washing with additional dichloromethane, and transferred to a reparatory funnel, whereupon it was diluted with additional water (300 mE). The layers were separated, and the organic layer was washed with water (500 mE) and 10% brine (200mE). The dichioromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with theproduct crystallizing during concentration. The suspension was filtered, and the solid was washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4-methyl-i -oxo- 1 ,3-dihydro-isobenzo- thran-5-yl ester. ?H NMR (400 MHz, CDC13): oe 7.87 (d,J=8.4 Hz, iH), 7.47 (d, J=8.4 Hz, iH), 5.32 (s, 2H), 2.41 (s,3H) | |
With triethylamine; In dichloromethane; at 3.8 - 10℃; for 1.08333h;Inert atmosphere; | 5-Hydroxy-4-methyl-3H-isobenzofuran-l-one (46.8 g, 285 mmol) was suspended in dichloromethane (935 mL) in 2-L roundbottom flask equipped with overhead stirrer under nitrogen. Triethylamine (59.5 mL, 427 mmol) was added and the reaction mixture was cooled in an ice bath to 3.8C. Trifluoromethanesulfonic anhydride (67.4 mL, 399 mmol) was added via addition funnel over 50 min, keeping the temperature < 10C. After stirring the reaction mixture for an additional 15 min, the reaction mixture was quenched with water (200 mL) and then stirred with DARCO KB (activated carbon, 25 g) for 15 min. The biphasic mixture was filtered over SOLKA FLOC, washing with additional dichloromethane, and transferred to a separatory funnel, whereupon it was diluted with additional water (300 mL). The layers were separated, and the organic layer was washed with water (500 mL) and 10% brine (200 mL). The dichloromethane solution was dried over sodium sulfate, filtered and evaporated. The orange-red solid was adsorbed onto silica gel (27.5 g) and eluted through a pad of silica gel (271 g) with 25% ethyl acetate/hexanes. The resulting solution was concentrated under vacuum with the product crystallizing during concentration. The suspension was filtered, the solid washed with heptane and dried under vacuum and nitrogen, providing trifluoromethanesulfonic acid 4- methyl-l-oxo-l,3-dihydro-isobenzofuran-5-yl ester. 1H NMR (400 MHz, CDC13 ): delta 7.87 (d, J = 8.4 Hz, 1H), 7.47 (d, J= 8.4 Hz, 1H), 5.32 (s, 2H), 2.41 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged A- bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 min then heated to 145 0C to obtain a homogeneous solution. The solution was aged at 145 0C for 2h? then the reaction mixture was cooled to 95 0C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through solka flok and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through solka flok and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgSO4, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing 5-hydroxy-4-memyl-3H-isobenzofuran-l-one. 1H NMR (400 MHz, DMSO-d6 ): delta 10.52 (s, IH), 7.51 (d, J- 8.3 Hz, IH), 6.99 (d, J= 8.3 Hz, IH), 5.28 (s, 2H), 2.07 (s, 3H). | ||
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 minutes then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2hours, then the reaction mixture was cooled to 95 C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 hours. The reaction was cooled to RT then the solids filtered through Solka- Flok powdered cellulose and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in the bottom of the flask. The DMF/EtOAc suspension was filtered through Solka-Flok powdered cellulose and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgSO4, filtered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vacuum at RT, providing 5-hydroxy-4-methyl-3H-isobenzofuran- 1 -one.1H NMR (400 MHz, DMSO-d6 ): delta 10.52 (s, 1H), 7.51 (d, J= 8.3 Hz, 1H), 6.99 (d, J- 8.3 Hz, 1H), 5.28 (s, 2H), 2.07 (s, 3H). | ||
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 minutes and then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2 hours, and then the reaction mixture was cooled to 95 C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 hours. The reaction was cooled to room temperature, the solids filtered through Solka-Flok powdered cellulose and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through Solka-Flok and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgS04, filtered and evaporated. The solids were slurried in 250 mL MTBE at room temperature, and then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at room temperature, providing 5-hydroxy-4-methyl-3H-isobenzofuran-l-one.1H NMR (400 MHz, DMSO-d6 ): 5 10.52 (s, 1H), 7.51 (d, J= 8.3 Hz, 1H), 6.99 (d, J= 8.3 Hz, 1H), 5.28 (s, 2H), 2.07 (s, 3H). |
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 min then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2h, then the reaction mixture was cooled to 95 C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through solka flok and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through solka flok and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3 x 500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgS04, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing 5-hydroxy-4-methyl-3H-isobenzofuran- 1 -one. | ||
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 minutes and then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2 hours, and then the reaction mixture was cooled to 95 C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 hours. The reaction was cooled to room temperature and then the solids filtered through Solka-Flok powdered cellulose and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in the bottom of the flask. The DMF/EtOAc suspension was filtered through Solka Flok and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgS04, fitered and evaporated. The solids were slurried in 250 mL MTBE at room temperature and then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at room temperature, providing 5-hydroxy-4-memyl-3H-isobenzofuran-l-one. ]U NMR (400 MHz, DMSO-d6 ): delta 10.52 (s, 1H), 7.51 (d, J= 8.3 Hz, 1H), 6.99 (d, J= 8.3 Hz, 1H), 5.28 (s, 2H), 2.07 (s, 3H). | ||
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 min then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2h, then the reaction mixture was cooled to 95 C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through solka flok and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through solka flok and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgS04, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing 5- hydroxy-4-methyl-3H-isobenzofuran-l-one. 1H NMR (400 MHz, DMSO-d6 ): delta 10.52 (s, 1H), 7.51 (d, J= 8.3 Hz, 1H), 6.99 (d, J= 8.3 Hz, 1H), 5.28 (s, 2H), 2.07 (s, 3H). | ||
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl -2 -methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 min then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2h, then the reaction mixture was cooled to 95 C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through SOLKA FLOC and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through SOLKA FLOC and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgS04, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing 5-hydroxy-4-methyl-3H-isobenzofuran-l-one. 1H NMR (400 MHz, DMSO-d6 ): delta 10.52 (s, 1H), 7.51 (d, J= 8.3 Hz, 1H), 6.99 (d, J= 8.3 Hz, 1H), 5.28 (s, 2H), 2.07 (s, 3H). | ||
To a 2 L 3 neck fiask equipped with oyerhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), cucN (83.0 g, 921 mmol), and DMF (500 mL). The solution wassparged with N2 for 15 min then heated to 145 c to obtain a homogeneous solution. The solution was aged at 145 c for 2h, then the reaction mixture was cooled to 95 c. 41.5 m water was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through SOLKA FLOK and the cake washed with 50 mL DMF. To a 3 L fiask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of fiask. The DMF/EtOAc suspension was filtered through SOLKA FLOK and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution(3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried oyer Mg504, fitered and eyaporated. The solids were siurried in 250 mL MTBE atRT then filtered and washed with 100 mL MTBE. The solids were dried under yaccum at RT, proyiding 5-hydroxy-4-methyl-3H-isobenzofuran-1-one. lH NMR (400 MHz, DMSO-d6):10.52 (s, 1H), ?7.51 (d, J= 8.3 Hz, 1H), 6.99 (d, J= 8.3 Hz, 1H), 5.28 (s, 2H), 2.07 (s, 3H). | ||
Step C: 5-hydroxy-4-methyl-3H-isobenzofuran-1-one: To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methylphenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 mm then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2h, then the reaction mixture was cooled to 95 C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through Solka-Floc and the cake washed with 50 mL DMF. To a 3 Lflask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through Solka-Floc and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over Mg504, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filteredand washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing 5- hydroxy-4-methyl-3H-isobenzofuran-1-one. ?H NMR (400 MHz, DMSO-d6): oe 10.52 (s, 1H), 7.51 (d,J= 8.3 Hz, 1H), 6.99 (d,J 8.3 Hz, 1H), 5.28 (s, 2H), 2.07 (s, 3H). | ||
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 mm then heated to 145 C to obtain a homogeneous solution. Thesolution was aged at 145 C for 2h, then the reaction mixture was cooled to 95 C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through SOLKA FLOC and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through SOLKA FLOC and thecake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3 x 500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over Mg504, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing 5 -hydroxy-4-methyl-3H-isobenzofuran- 1-one. | ||
Step C: 5-Hydroxy-4-methyl-3H-isobenzofuran-l-one: To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 min then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2h, then the reaction mixture was cooled to 95 C. 41.5 mL of water was added (sparged with N2), and the reaction was aged for 20 h. The reaction was cooled to RT then the solids filtered through SOLKA FLOC and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through SOLKA FLOC and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgS04, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing 5-hydroxy-4-methyl-3H-isobenzofuran-l-one. | ||
Step C: 5-Hydroxy-4-methyl-3H-isobenzofuran-l-one: To a 2 L 3 neck flask equipped with overhead stirrer, 2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with 2 for 15 min then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2h, then the reaction mixture was cooled to 95 C. 41.5 mL of water was added (sparged with N2), and the reaction was aged for 20 h. The reaction was cooled to RT then the solids filtered through SOLKA FLOC and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through SOLKA FLOC and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgS04, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing 5-hydroxy-4-methyl-3H-isobenzofuran-l-one. | ||
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol) , CuCN (83.0 g, 921 mmol) , and DMF (500 mL) . The solution was sparged with N2 for 15 min then heated to 145 to obtain a homogeneous solution. The solution was aged at 145 for 2h, then the reaction mixture was cooled to 95 . 41.5 mL water was added (sparged with N2) , and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through SOLKA-and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through SOLKA-and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 brine solution (3x500 mL) . The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgSO4, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vacuum at RT, providing 5-hydroxy-4-methyl-3H-isobenzofuran-1-one. 1H NMR (400 MHz, DMSO-d6 ) : delta 10.52 (s, 1H) , 7.51 (d, J 8.3 Hz, 1H) , 6.99 (d, J 8.3 Hz, 1H) , 5.28 (s, 2H) , 2.07 (s, 3H) . | ||
To a 2 L 3 neck flask equipped with overhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 min then heated to 145C to obtain a homogeneous solution. The solution was aged at 145C for 2h, then the reaction mixture was cooled to 95C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled to rt then the solids filtered through SOLKA FLOK and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through SOLKA FLOK and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgS04, fitered and evaporated. The solids were slurried in 250 mL MTBE at rt then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at rt, providing 5- hydroxy-4-methyl-3H-isobenzofuran-l-one. 1H MR (400 MHz, DMSO-d6 ): delta 10.52 (s, 1H), 7.51 (d, J= 8.3 Hz, 1H), 6.99 (d, J= 8.3 Hz, 1H), 5.28 (s, 2H), 2.07 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; | Step A: tert-Butyl 4- { [(4-methyl- 1 -oxo- 1 ,3-dihydro-2-benzofuran-5-yl)oxylmethyl|piperidine- 1-carboxylate 5- Hydroxy-4-methyl-2-benzofuran-l(3H)-one (80 mg, 0.49 mmol) and tert-butyl 4- (bromomethyl)piperidine-l-carboxylate (200 mg, 0.72 mmol) were mixed together in DMF (5 mL). Potassium carbonate (140 mg, 0.98 mmol) was added and the mixture was stirred at 80 C overnight. The reaction was diluted with EtOAc and water and the layers separated. The organic phase was washed with brine, dried (Na2S04), filtered and concentrated. The resulting residue was purified by MPLC (0-50% EtOAc/Hexane) to provide tert-butyl 4- { [(4-methyl- 1 -oxo- 1,3- dihydro-2-benzomran-5-yl)oxy]methyl} piperidine- 1 -carboxylate. 1H NMR (500 MHz, CDC13), delta 7.74 (d, J= 8.4 Hz, 1H), 6.96 (d, J= 8.4 Hz, 1H), 5.20 (s, 2H), 4.19 (m, 2 H), 3.92 (d, J = 6.2 Hz, 2H), 2.77 (m, 2H), 2.16 (s, 3H), 2.06-2.00 (m, 1H), 1.83 (d, J = 13.1 Hz, 2H), 1.47 (s, 9 H), 1.40-1.28 (m, 2 H). LC-MS (IE, m/z): 384 [M + 23]+. | |
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; | 5-Hydroxy-4-methyl-2-benzofuran-1(3H)-one (80 mg, 0.49 mmol) and tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (200 mg, 0.72 mmol) were mixed together in DMF (5 mL). Potassium carbonate (140 mg, 0.98 mmol) wasadded and the mixture was stirred at 80 C overnight. The reaction was diluted with EtOAc and water and the layersseparated. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residuewas purified by MPLC (0-50% EtOAc/Hexane) to provide tert-butyl 4-[(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)oxy]methyl}piperidine-1-carboxylate.1H NMR (500 MHz, CDCl3), delta 7.74 (d, J= 8.4 Hz, 1H), 6.96 (d, J= 8.4 Hz, 1H), 5.20 (s, 2H), 4.19 (m, 2 H), 3.92 (d, J =6.2 Hz, 2H), 2.77 (m, 2H), 2.16 (s, 3H), 2.06-2.00 (m, 1H), 1.83 (d, J = 13.1 Hz, 2H), 1.47 (s, 9 H), 1.40-1.28 (m, 2 H).LC-MS (IE, m/z): 384 [M + 23]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(I) cyanide; In N,N-dimethyl-formamide; at 145℃;Inert atmosphere; | Step C: 5-Hydroxy-4-methyl-3H-isobenzofuran-1-one; To a 2 L 3 neck flask equipped withoverhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution wassparged with N2 for 15 min then heated to 145 C to obtain a homogeneous solution. Thesolution was aged at 145 C for 2h, then the reaction mixture was cooled to 95 C. 41.5 mLwater was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled toRT then the solids filtered through solka flok and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottomof flask. The DMF/EtOAc suspension was filtered through solka flok and the cake was washedwith 250 mL EtOAc. The resulting filtrate was washed with 5% brine solution (3 x 500 mL).The aqueous layers were extracted with 500 mL EtOAc and the combined organics were driedover MgS04, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing5-hydroxy-4-methyl-3H-isobenzofuran-1-one. | |
With copper(l) cyanide; In N,N-dimethyl-formamide; at 95 - 145℃; for 22.25h;Inert atmosphere; | Step C: 5-Hydroxy-4-methyl-3H-isobenzofuran-1-one: To a 2 L 3 neck flask equipped withoverhead stirrer, N2 inlet, and condenser were charged 4-bromo-3-hydroxymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL). The solution was sparged with N2 for 15 mm then heated to 145 C to obtain a homogeneous solution. The solution was aged at 145 C for 2h, then the reaction mixture was cooled to 95 C. 41.5 mL water was added (sparged with N2), and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through solka flok and the cake washed with 50 mL DMF. To a 3 L flask containing 1 L EtOAc was added the DMF filtrate. A precipitate coating formed in bottomof flask. The DMF/EtOAc suspension was filtered through solka flok and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3 x 500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgSO4, fitered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vaccum at RT, providing5-hydroxy-4-methyl-3H-isobenzofuran-1-one | |
With copper(l) cyanide; In N,N-dimethyl-formamide; at 145℃; for 2h;Inert atmosphere; | 4-Bromo-3 -hydro xymethyl-2-methyl phenol (100 g, 461 mmol), CuCN (83.0 g, 921 mmol), and DMF (500 mL) were charged to a 2 L 3 -neck flask equipped with overhead stirrer, N2 inlet, and condenser. The solution was sparged with N2 for 15 min then heated to 145C to obtain a homogeneous solution. The solution was aged at 145C for 2h and then the reaction mixture was cooled to 95C. 41.5 mL of water was added (sparged with N2) and the reaction aged for 20 h. The reaction was cooled to RT then the solids filtered through SOLKA FLOC and the cake washed with 50 mL DMF. The filtrate from the DMF was added to a 3 L flask containing 1 L EtOAc. A precipitate coating formed in bottom of flask. The DMF/EtOAc suspension was filtered through SOLKA FLOC and the cake was washed with 250 mL EtOAc. The resulting filtrate was washed with 5 % brine solution (3x500 mL). The aqueous layers were extracted with 500 mL EtOAc and the combined organics were dried over MgS04, filtered and evaporated. The solids were slurried in 250 mL MTBE at RT then filtered and washed with 100 mL MTBE. The solids were dried under vacuum at RT, providing 5-hydroxy-4-methyl-3H-isobenzofuran-l-one. 1H NMR (400 MHz, DMSO-d6 ): delta 10.52 (s, 1H), 7.51 (d, J= 8.3 Hz, 1H), 6.99 (d, J= 8.3 Hz, 1H), 5.28 (s, 2H), 2.07 (s, 3H). |
Tags: 1194700-73-6 synthesis path| 1194700-73-6 SDS| 1194700-73-6 COA| 1194700-73-6 purity| 1194700-73-6 application| 1194700-73-6 NMR| 1194700-73-6 COA| 1194700-73-6 structure
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