反应详情

To a solution of methyl 3-hydroxybenzoate (500 mg) in dimethylformamide (5 ml), 0.463 ml of 2-bromopropane and 197 mg of sodium hydride were added under ice-cooling, and the reaction solution was stirred at room temperature for 5 hours. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of lithium aluminum hydride (250 mg) in tetrahydrofuran (3 ml), a solution of the crude product in tetrahydrofuran (2 ml) was added under ice-cooling, and the reaction solution was stirred at room temperature for 1 hour. To the reaction solution was added sodium sulfate decahydrate, and the mixture was stirred at the same temperature for 1 hour. The reaction solution was Celite-filtered, and the filtrate was distilled off under reduced pressure. The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-30:70)) to afford the title compound as a colorless oil.

1. temperaturecooling
2. extractionthe mixture was extracted with ethyl acetate
3. washThe combined organic layers were washed with a saturated saline solution
4. dry with materialdried over anhydrous sodium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customto afford a crude product as a yellow oil
7. temperaturecooling
8. stirringthe reaction solution was stirred at room temperature for 1 hour
9. stirringthe mixture was stirred at the same temperature for 1 hour
10. filtrationThe reaction solution was Celite-filtered
11. distillationthe filtrate was distilled off under reduced pressure
12. customThe residue obtained
13. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-30:70))