Hydrochloric Acid → 2-Fluoro-3-(4-propylcyclohexyl)propan-1-ol

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Reaction Steps

To a reaction vessel under a nitrogen atmosphere, 0.3 g of lithium aluminum hydride and 10 ml of THF were added, and the resultant mixture was cooled to −10° C. Thereto, 1.1 g of ethyl 2-fluoro-3-(4-propylcyclohexyl)propanoate (e-11) dissolved in 10 ml of THF was added dropwise in a temperature range of −10° C. to 0° C. Then, the resultant mixture was heated to 25° C., and stirred for 1 hour. Subsequently, 100 ml of 1 N HCl aqueous solution and 100 ml of ethyl acetate were added to separate the mixture into an organic layer and an aqueous layer, and an extraction operation was performed. The resultant organic layer was isolated, and washed with water, and then the resultant solution was dried over anhydrous magnesium sulfate. The resultant solution was concentrated under reduced pressure, the resultant residue was purified by a preparative isolation operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=5:1 in a volume ratio) as an eluent and silica gel as a filler, the resultant product was dried, and thus 0.68 g of 2-fluoro-3-(4-propylcyclohexyl)propan-1-ol (e-12) was obtained. A yield based on compound (e-11) was 75.7%.

Provenance & Evidence