Ammonium Chloride → (1s,4s)-4-(3-Fluorophenyl)cyclohexanol

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Reaction Conditions

Reaction Steps

Sodium borohydride (9.8 g) and THF (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to 0° C. The compound (19) (47.2 g) dissolved in THF (100 ml) was added dropwise thereto, with caution in the evolution of hydrogen gas, and the mixture was stirred for 3 hours. A saturated aqueous solution of ammonium chloride (400 ml) and ethyl acetate (400 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed with brine, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene: ethyl acetate=10:1 by volume) as an eluent and silica gel as a stationary phase powder, and dried, giving 40.9 g of 4-(3-fluorophenyl)cyclohexanol (20). The yield based on the compound (19) was 85.7%.

Provenance & Evidence