反应详情

To a solution of 2-phenoxybenzaldehyde (535 mg) in tetrahydrofuran (5 ml), 0.326 ml of diiodomethane and 5.4 ml of methyllithium (1.0M diethyl ether solution) were added under ice-cooling, and the reaction solution was stirred at the same temperature for 30 minutes and then at room temperature for 1 hour. To the reaction solution was added water, 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 the crude product in tetrahydrofuran (5 ml), 284 mg of sodium cyanoborohydride and 0.569 ml of trifluoroborane-diethyl ether complex were added under ice-cooling, and the reaction solution was stirred at the same temperature for 50 minutes. To the reaction solution was added a saturated saline solution, 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, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50/50)) to afford the title compound as a colorless oil.

1. temperaturecooling
2. waitat room temperature for 1 hour
3. extractionthe mixture was extracted with ethyl acetate
4. washThe combined organic layers were washed with a saturated saline solution
5. dry with materialdried over anhydrous sodium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. customto afford a crude product as a yellow oil
8. temperaturecooling
9. stirringthe reaction solution was stirred at the same temperature for 50 minutes
10. additionTo the reaction solution was added a saturated saline solution
11. extractionthe mixture was extracted with ethyl acetate
12. washThe combined organic layers were washed with a saturated saline solution
13. dry with materialdried over anhydrous sodium sulfate
14. distillationThe solvent was distilled off under reduced pressure
15. customthe residue obtained
16. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50/50))