Structure of 103262-35-7
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CAS No. : | 103262-35-7 |
Formula : | C9H10O2 |
M.W : | 150.17 |
SMILES Code : | OCC1=CC=C2OCCC2=C1 |
MDL No. : | MFCD02169755 |
InChI Key : | XQDNBMXUZGAWSZ-UHFFFAOYSA-N |
Pubchem ID : | 2776158 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
* 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 sodium borohydrid; In methanol; | Reference Example 79 (2,3-dihydrobenzofuran-5-yl)methanol To a solution of 2,3-dihydrobenzofuran-5-carbaldehyde (30.0 g, 0.202 mol) in methanol (150 mL) was added sodium borohydride (3.83 g, 0.101 mol) under ice-cooling. The mixture was stirred for 15 minutes at ambient temperature and then diluted with water. The product was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to afford the title compound (yield 27.6 g, 91%) as an oily product. NMR (CDCl3) δ: 1.67 (1H, s), 3.20 (2H, t, J 8.6 Hz), 4.57 (2H, t, J=8.6 Hz), 4.58 (2H, s), 6.76 (1H, d, J=8.0 Hz), 7.10 (1H, d, J=8.0 Hz), 7.22 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | Reference Example 80 5-bromomethyl-2,3-dihydrobenzofuran To a solution of <strong>[103262-35-7](2,3-dihydrobenzofuran-5-yl)methanol</strong> (29.0 g, 0.193 mol) in tetrahydrofuran (150 mL) was added phosphorous tribromide (34.8 g, 0.129 mol) under ice/salt-cooling. The mixture was stirred for 20 minutes and then poured into water. The mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated to afford the title compound (yield 27.6 g, 91%). m.p.: 57-60 C.; NMR (CDCl3) δ: 3.20 (2H, t, J=8.8 Hz), 4.51 (2H, s), 4.59 (2H, t, J=8.8 Hz), 6.73 (1H, d, J=8.2 Hz), 7.14 (1H, d, J=8.2 Hz), 7.24 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; In dichloromethane; ethyl acetate; | Reference Example 14-1 (2,3-dihydrobenzo[b]furan-5-yl)methyl chloride To a solution of <strong>[103262-35-7](2,3-dihydrobenzo[b]furan-5-yl)methanol</strong> (1.5 g, 10 mmol) in dichloromethane (10 mL) were added under ice-cooling triethylamine (1.67 mL, 12 mmol) and methanesulfonyl chloride (0.85 mL, 10 mmol) and the mixture was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (1.6 g, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogenchloride; In tetrahydrofuran; methanol; | Reference Example 13-1 (2,3-dihydrobenzo[b]furan-5-yl)methanol To a solution of 2,3-dihydrobenzo[b]furan-5-carboxylic acid (1.64 g, 10 mmol) in tetrahydrofuran (10 mL) was added under ice-cooling lithium aluminum hydride (949 mg, 25 mmol) and the mixture was stirred at 60C for 1 h. The reaction mixture was stirred under ice-cooling and methanol and 1N hydrochloric acid were added. The precipitate was filtered off and the mother liquor was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (1.5 g, 100%). |
With lithium aluminium tetrahydride; In tetrahydrofuran; at -8 - 20℃; for 3.0h; | (1) Dissolve dihydrobenzofuran-5-carboxylic acid in anhydrous tetrahydrofuran to obtain solution A. Under temperature of -8 deg.C ~ -6 deg.C, Dropwise adding lithium aluminum hydride to solution A to obtain reaction system A, Warm reaction system A to room temperature uniformly, React for 3h under stirring conditions, Then placed in an ice-water bath to dropwise add ice-water to quench until no bubbles are generated. Add tetrahydrofuran solvent, wash the filtrate 3 times with dichloromethane, and then wash the filtrate with saturated brine. Filter and distill off the solvent under reduced pressure to obtain dihydrobenzofuran-5-methanol; where the mass-volume ratio of dihydrobenzofuran-5-carboxylic acid to anhydrous tetrahydrofuran in reaction system A is 1:20, The molar ratio of hydrobenzofuran-5-carboxylic acid to lithium aluminum hydride is 1: 2.5; the drop acceleration rate of lithium aluminum hydride is 1 g / min; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 24.0h; | To Cpd 8c (0.3 g, 1.07 mmol) in tetrahydrofuran was added <strong>[103262-35-7]2,3-dihydro-1-benzofuran-5-ylmethanol</strong> (0.16 g, 1.07 mmol), triphenylphosphine (0.57 g, 2.15 mmol) and diethyl azodicarboxylate (0.22 g, 1.29 mmol). The reaction was stirred at room temperature for 24 h. The reaction mixture was taken up in ethyl acetate, washed with water, and the phases were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting material was purified by normal phase chromatography using an ISCO automated system to give Cpd 8d. | |
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 24.0h; | To Cpd 8c (0.3 g, 1.07 mmol) in tθtrahydrofuran was added <strong>[103262-35-7]2,3-dihydro-1-benzofuran-5-ylmethanol</strong> (0.16 g, 1.07 mmol), triphenylphosphine (0.57 g, 2.15 mmol) and diethyl azodicarboxylate (0.22 g, 1.29 mmol). The reaction was stirred at room temperature for 24 h. The reaction mixture was taken up in ethyl acetate, washed with water, and the phases were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting material was purified by normal phase chromatography using an ISCO automated system to give Cpd 8d. | |
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 24.0h; | To Cpd 8c (0.3 g, 1.07 mmol) in tetrahydrofuran was added <strong>[103262-35-7]2,3-dihydro-1-benzofuran-5-ylmethanol</strong> (0.16 g, 1.07 mmol), triphenylphosphine (0.57 g, 2.15 mmol) and diethyl azodicarboxylate (0.22 g, 1.29 mmol). The reaction was stirred at room temperature for 24 h. The reaction mixture was taken up in ethyl acetate, washed with water, and the phases were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting material was purified by normal phase chromatography using an ISCO automated system to give Cpd 8d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; | To compound 18d (2.8 g, 8.9 mmol) in 100 mL of THF was added DIAD (2.1 mL, 10.7 mmol), triphenyl phosphine (17.8 mmol), and compound Xxa. The mixture was allowed to stir at rt under an atmosphere of Argon. The mixture was concentrated, diluted with EtOAc, and washed with water. The organic phase was partitioned, dried over MgSO4, filtered, and the filtrate was concentrated to a yellow oil. The oil was purified by reverse-phase chromatography to furnish compound XXb. | |
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Inert atmosphere; | To compound 18d (2.8 g, 8.9 mmol) in 100 mL of THF was added DIAD (2.1 mL, 10.7 mmol), triphenyl phosphine (17.8 mmol), and <strong>[103262-35-7]2,3-dihydro-1-benzofuran-5-ylmethanol</strong>. The mixture was allowed to stir at rt under an atmosphere of Argon. The mixture was concentrated, diluted with EtOAc, and washed with water. The organic phase was partitioned, dried over MgSO4, filtered, and the filtrate was concentrated to a yellow oil. The oil was purified by reverse-phase chromatography to furnish compound 32a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; | To compound 18d (2.8 g, 8.9 mmol) in 100 mL of THF was added DIAD (2.1 mL, 10.7 mmol), triphenyl phosphine (17.8 mmol), and compound Xxa. The mixture was allowed to stir at rt under an atmosphere of Argon. The mixture was concentrated, diluted with EtOAc, and washed with water. The organic phase was partitioned, dried over MgSO4, filtered, and the filtrate was concentrated to a yellow oil. The oil was purified by reverse-phase chromatography to furnish compound XXb. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 0℃; | (2) Under the condition of 0 C, add dihydrobenzofuran-5-methanol from step (1) and triethylamine to a dichloromethane solvent, Stir for 5min, Then add methanesulfonyl chloride dropwise to obtain reaction system B, Reaction system B was stirred for 0.5 h,Water was added dropwise to quench, and then saturated brine was added, and extracted with dichloromethane. The organic phase was dried, filtered, and the solvent was distilled off under reduced pressure to obtain the mesylate. The molar ratio of amine and methylsulfonyl chloride is 1: 1.2: 3, and the mass-to-volume ratio g of dihydrobenzofuran-5-methanol to dichloromethane solvent is 1:20; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With acetic anhydride; acetic acid; In dimethyl sulfoxide; at 60℃; for 0.25h;Microwave irradiation; Green chemistry; | 7a (0.67mmol, 0.1g), DMSO 2.05mL, Ac2O 1.43mL, AcOH 0.26mL were successively added to a 15mL microwave reaction tube, the microwave power was 150w, the heating temperature was 60C, and the reaction time was 15min.After cooling, NaHCO3 solution was added and stirred at room temperature for 30 min. Extract with ethyl acetate, collect the organic phase, and extract the aqueous phase with ethyl acetate 2-3 times.The organic phases were combined, washed with water in sequence, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the target product 7b (yield: 65%). |
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