Sodium Hydroxide → 3-((Tert-butyldiphenylsilyl)oxy)-2-fluoropropan-1-OL

Participants

Reaction Steps

3-{[Tert-butyl(diphenyl)silyl]oxy}-2-fluoropropionic acid ethyl ester (17.98 g, 48.01 mmol) was dissolved in tetrahydrofuran (250 ml). Lithium borohydride (2.32 g, 96.02 mmol) was added to the solution under cooling on ice and the mixture was stirred for 24 hours. To the reaction solution was added 1N sodium hydroxide aqueous solution under cooling on ice to quench the reaction. The resulting solution was extracted with ethyl acetate, and the resultant was washed with saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 12.10 g (76%) of the title compound in the form of a colorless clear oily product.

Provenance & Evidence