反应详情

To a solution of 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}-2-phenylethoxy)-3-fluorocyclohexanol (8.46 g, 22.9 mmol) in dichloromethane (100 mL) at 0° C. was added methanesulfonyl chloride (2.49 mL, 32.1 mmol) and diisopropylethylamine (11.1 mL, 64.1 mmol). The reaction mixture was stirred for 1 min, diluted with dichloromethane and washed with 5% potassium bisulfate. The layers were separated and the aqueous extracted with dichloromethane (3×). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography (hexane: ethyl acetate 70:30) gave 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}-2-phenylethoxy)-3-fluorocyclohexyl methanesulfonate (9.77 g, 100% yield) as a clear oil.

1. washwashed with 5% potassium bisulfate
2. customThe layers were separated
3. extractionthe aqueous extracted with dichloromethane (3×)
4. washThe combined organic layers were washed with water and brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by flash column chromatography (hexane: ethyl acetate 70:30)