Sodium hydride → 2-[4-(4-Cyclohexyl-3-trifluoromethyl-benzylsulfanyl)-phenyl]-[1,3]dioxane

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Reaction Conditions

Reaction Steps

Crude 4-[1,3]dioxan-2-yl-benzenethiol (0.9 mmol) is dissolved in DMF (15 mL, anhydrous). The solution is cooled to 0° C. followed by addition of NaH (76 mg, 1.8 mmol). After stirring for 30 min, the 4-bromomethyl-1-cyclohexyl-2-trifluoromethyl-benzene prepared above (0.8 mmol) dissolved in DMF (2 mL) is added dropwise via syringe. The mixture is stirred for 1 h, then poured into a mixture of ice and saturated aqueous NH4Cl. The aqueous phase is extracted with diethyl ether (3×30 mL). The combined organic layers are washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated. The residue obtained is purified by silica gel chromatography (10% ethyl acetate in hexanes) to give 2-[4-(4-cyclohexyl-3-trifluoromethyl-benzylsulfanyl)-phenyl]-[1,3]dioxane as white solid.

Provenance & Evidence