反应详情

2-Iodoacetophenone (6.30 g) was dissolved in methanol (50 ml), sodium borohydride (726 mg) was added and the mixture was stirred at room temperature for 1.5 hr. 10% Aqueous citric acid was added to the reaction mixture and ethanol was evaporated. Water was added and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and brine, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was dissolved in tetrahydrofuran (50 ml). The solution was cooled to 0° C., sodium hydride (1.54 g, 60% in oil), (R)-glycidyl nosylate (9.95 g) and dimethyl sulfoxide (10 ml) were successively added, and the mixture was stirred overnight at 0° C.—room temperature. 10% Aqueous citric acid was added to neutralize the reaction mixture, and extracted 3 times with ethyl acetate. The organic layer was washed successively with water (twice) and brine, and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (6.36 g).

1. customwas evaporated
2. additionWater was added
3. extractionthe mixture was extracted 3 times with ethyl acetate
4. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and brine
5. dry with materialdried over sodium sulfate
6. concentrationThe organic layer was concentrated under reduced pressure
7. dissolutionthe obtained residue was dissolved in tetrahydrofuran (50 ml)
8. temperatureThe solution was cooled to 0° C.
9. additionsodium hydride (1.54 g, 60% in oil), (R)-glycidyl nosylate (9.95 g) and dimethyl sulfoxide (10 ml) were successively added
10. stirringthe mixture was stirred overnight at 0° C.—room temperature
11. addition10% Aqueous citric acid was added
12. extractionextracted 3 times with ethyl acetate
13. washThe organic layer was washed successively with water (twice) and brine
14. dry with materialdried over sodium sulfate
15. concentrationThe organic layer was concentrated under reduced pressure
16. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)