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Structure of 1255206-68-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1255206-68-8 |
Formula : | C11H10O3 |
M.W : | 190.20 |
SMILES Code : | O=C1OCC2=C1C=CC(C3OC3)=C2C |
MDL No. : | MFCD18434504 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H312-H302-H315-H319-H361-H372-H317-H351-H335-H412 |
Precautionary Statements: | P501-P273-P272-P260-P270-P202-P201-P271-P264-P280-P312-P337+P313-P305+P351+P338-P362+P364-P333+P313-P302+P352+P312-P304+P340+P312-P403+P233-P405 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
In dimethyl sulfoxide; at 150℃; for 1h;Microwave irradiation; | A mixture of 4-methyl-5 -oxiran-2-yl-2-benzofuran- 1 (3H)-one (700 mg, 3.68 mmol) and 1,1- dimethylethyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate (748 mgs 3.68 mmol) in 2 mL DMSO was heated under microwave condition (15O0C) for 1 hr. After cooling to rt, the mixture was diluted with water (50 mL), extracted with EtOAc (3 X 50 mL). The combined organic layers were washed with brine and dried over Na2SO45 then concentrated. The residue was purified by TLC (MeOHZDCM=I : 15) to obtain l,l-dimethylethyl5-[2-hydroxy-2-(4-methyl-l-oxo-l,3- dihydro-2-benzofuran-5-yl)ethyl]-2,5-diazabicyclo[2.2.2]octane-2-carboxylate as a mixture of 4 isomers, which was separated by SFC chiral chromatography to obtain four chiral isomers or isomer mixtures A, B, C and D with the same MS m/z 403 (M+l)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5-ethenyI-4-methyl-2-benzofuran-l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 0C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 12Og Redi-sep column eluting with 0- 80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3/i)- one. 1H-NMR (500 MHz5 CDCl3): δ ppm 7.77 ( d5 J= 8 Hz, IH), 7.43 (d, J= 8 Hz, IH), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, IH) , 2.43 (s, 3H). LC-MS: MH-I=I 91; tR = 2.2 min | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0C then meta-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, saturated sodium bicarbonate, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5-oxiran-2-yl-2- benzofuran-1 (3H)-one.Ή-NMR (500 MHz, CDC13): δ ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J = 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.74 (dd, J= 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H).LC-MS: [M+l] =191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5-emenyl-4-memyl-2-benzofuran-l(3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0 C then meia-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, saturated sodium bicarbonate, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5- oxiran-2-yl-2-benzofuran- 1 (3H)-one.Ή-NMR (500 MHz, CDC13): 6 ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.74 (dd, J= 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H).LC-MS: [M+1] =191. |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | Step D: 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one5-ethenyl-4-methyl-2-benzofuran-l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then m-CPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0- 80% EtOAc/hexane solvent system to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. Ή- NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | Step D: 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one5-ethenyl-4-methyl-2-benzofuran-l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then m-CPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0- 80% EtOAc/hexane solvent system to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H- NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5 -Ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC through a 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H); LC-MS: M+l=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | Step B: 4-Methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one 5-ethenyl-4-methyl-2-benzofuran-l(3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0 C then meto-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, saturated sodium bicarbonate, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.74 (dd, J= 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5-ethenyl-4-memyl-2-benzofuran-l(3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0 C then meta-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, saturated sodium bicarbonate, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyI-5- oxiran-2-yl-2-benzofuran- 1 (3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.74 (dd, J= 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: [M+l] =191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; | 4-methyl-5-oxiran-2-yl-2-benzofuran-1 (3H)-one; 5-Ethenyl-4-methyl-2-benzofuran-1(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at R T overnight. The reaction mixture was washedonce each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLCthrough a 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yieldtarget 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz, CDCh): ()ppm 7.77( d, J= 8Hz, 1H), 7.43 (d, J= 8Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H),2.735 ( dd, J = 2.2, 5.5 Hz, 1H), 2.43 (s, 3H); LC-MS: M+1=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDCls): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+l=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5 -ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+l=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then m-CPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzomran-l(3H)-one. -NMR (500 MHz, CDCI3): δ ppm 7.77 ( d, J= 8 Hz, IH), 7.43 (d, J= 8 Hz, IH), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, IH) , 2.43 (s, 3H). LC-MS: M+l=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | Step B: 4-methyl-5-oxiran-2-yl-2-benzofuran- 1 (3Ff)-one: 5-Ethenyl-4-methyl-2-benzofuran-1(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stuffed at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC through a 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yieldtarget 4-methyl-5-oxiran-2-yl-2-benzofuran-1(31])-one. ‘H-NMR (500 MHz, CDC13): ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H) | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | <strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.46 g, 8.38 mmol) was added to DCM (25 mL) at O c then mcPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at RT oyernight. The reaction mixture was washedonce each with saturated aqueous Na25203, NaHcO3, and brine. The organie layer was driedoyer Na2504, filtered, and eyaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAclhexane solyent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz,CDC13): ppm „7.”7”7 (d, J= 8 Hz, 1H), „7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H) „ 2.43 (s, 3H). LC-MS: M+1=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | Step B: 4-methyl-5-oxiran-2-yl-2-benzofuran- 1 (311)-one: 5-ethenyl-4-methyl-2-benzofuran- 1(311)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g RediSep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1(311)-one. ‘H-NMR (500 MHz,CDC13): ö ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+1191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5 -ethenyl-4-methyl-2-benzofuran-1(311)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at RT overnight. The reaction mixture waswashed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer wasdried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-1(311)-one. lH-NMR (500 MHz, CDC13): ö ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27(t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H)2.43 (s, 3H). LC-MS: M+1191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 16h; | 5 -ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT 16 h. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2SC"4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-LC/MS: M+l=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | <strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C, mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RTovernight. The reaction mixture was washed once each with saturated aqueous Na25203, NaHCO3, and brine. The organic layer was dried over Na2504, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sepcolumn eluting with 0-80% EtOAc/hexane solvent system to yield the title compound. MS[M+H] = 191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | <strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C, mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated todryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield the title compound. MS[M+H]= 191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; | Step B: 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one: 5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C, then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous a2S203, aHC03, and brine. The organic layer was dried over a2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | Step B: 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one: 5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C, then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5-Ethenyl-4-methyl-2-benzofuran-1 (3H) -one (1.46g, 8.38 mmol) (INTERMEDIATE 30) was added to DCM (25 mL) at 0 then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g REDI-column eluting with 0-80EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1 (3H) -one. 1H NMR (500 MHz, CDCl3) : δ ppm 7.77 (d, J 8 Hz, 1H) , 7.43 (d, J 8 Hz, 1H) , 5.30 (s, 2 H) , 4.12 (s, 1 H) , 3.27 (t, J 4Hz, 1 H) , 2.735 (dd, J 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H) . LC-MS: M+1 191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | 5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at rt overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, j= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H), 2.43 (s, 3H). LC-MS: M+l=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; | 5-Ethenyl-4-methyl-2-benzofuran-1(3H)-one (1.46 g, 8.38mmol) was added to DCM (25 mL) at 0 C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirredat RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, andbrine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purifiedby MPLC through a 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz, CDCl3): δ ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz,1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H), 2.43 (s, 3H); LC-MS: M+1=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; | Step B: 4-methyl-S -oxiran-2-yl-2-benzofuran- 1 (311)-one: 5-ethenyl-4-methyl-2-benzofuran-1(311)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0C then mCPBA (2.89 g, 16.8mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washedonce each with saturated aqueous Na25203, NaHCO3, and brine. The organic layer was driedover Na2504, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-1(31])-one. ‘H-NMR (500 MHz, CDC13): ö ppm 7.77 (d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1 H), 3.27 (t,J= 4Hz, 1 H), 2.735 (dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+1=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; | 5-ethenyl-4-methyl-2-benzofuran- 1 (3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mE) at 0 C. then metachioroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was washed once each with saturated aqueous Na25203, saturated sodium bicarbonate, and brine.The organic layer was dried over Na2504, filtered, and evaporated to dryness. The crude material was purified by MPEC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5-oxiran-2-yl-2-benzo-furan-1(3H)-one.‘H-NMR (500 MHz, CDC13): ö ppm 7.77 (d, J=8 Hz, 1H), 7.43 (d, J=8 Hz, 1H), 5.30 (s, 2H), 4.12 (s, 1H), 3.27 (t, J=4 Hz, 1H), 2.74 (dd, J=2.2, 5.5 Hz, 1H), 2.43 (s, 3H).EC-MS: [M+1]=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;Inert atmosphere; | 5-ethenyl-4-methyl-2-benzofuran- l(3H)-one (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0C then mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S203, NaHC03, and brine. The organic layer was dried over Na2S04, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120g RediSep column eluting with 0-80% EtOAc/hexane solvent system to yield target 4-methyl-5-oxiran-2-yl-2-benzofuran-l(3H)-one. 1H-NMR (500 MHz, CDC13): δ ppm 7.77 ( d, J= 8 Hz, 1H), 7.43 (d, J= 8 Hz, 1H), 5.30 (s, 2 H), 4.12 ( s, 1 H), 3.27 (t, J= 4Hz, 1 H), 2.735 ( dd, J = 2.2, 5.5 Hz, 1H) , 2.43 (s, 3H). LC-MS: M+l=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | <strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0 C., mCPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120 g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield the title compound. MS [M+H]+=191. | |
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; | [0238] <strong>[1255206-69-9]5-ethenyl-4-methyl-2-benzofuran-1(3H)-one</strong> (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0 C then meta-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at RT overnight. The reaction mixturewas washed once each with saturated aqueous Na2S2O3, saturated sodium bicarbonate, and brine. The organic layerwas dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography(eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. 1H-NMR(500 MHz, CDCl3): δ ppm 7.77 (d, J=8 Hz, 1H), 7.43 (d, J = 8 Hz, 1H), 5.30 (s, 2 H), 4.12 (s, 1H), 3.27 (t, J = 4Hz, 1 H),2.74 (dd, J = 2.2, 5.5 Hz, 1H), 2.43 (s, 3H).LC-MS: [M+1] =191. |