Water → 4-[2-Fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-4'-propoxybicyclohexane

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Reaction Conditions

Reaction Steps

The compound (15) (8.2 g), dimethyl sulfoxide (40 ml) and sodium hydride (1.0 g) were put in a reaction vessel under a nitrogen atmosphere, and heated to 60° C. The stirring was continued for 1 hour, and then a dimethyl sulfoxide solution in which 1-bromopropane (16) (2.6 g) was dissolved in dimethyl sulfoxide (5 ml) was added dropwise thereto, and the mixture was heated to 120° C. The stirring was continued for 2 hours, and then the mixture was cooled slowly to room temperature, and water (200 ml) and toluene (200 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into two phases, the organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed sequentially with water and a saturated aqueous solution of sodium hydrogencarbonate and 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 toluene as an eluent and silica gel as a stationary phase powder, and further purified by means of recrystallization from a mixed solvent of heptane and Solmix (heptane: Solmix=1:1 by volume) and dried, giving 2.8 g of 4-[2-fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-4′-propoxybicyclohexane (No. 54). The yield based on the compound (12) was 31.4%.

Provenance & Evidence