Ammonium Chloride → Methyl 4-[cyclohexyl(5-cyclohexyl-2-ethylthiophen-3-yl)methoxy]benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-[(5-bromo-2-ethylthiophen-3-yl)(cyclohexyl)methoxy]benzoate (1.20 g) synthesized above in N-methylpyrrolidone (30 mL) were added 0.5M cyclohexylzinc bromide-tetrahydrofuran solution (8.22 mL) and bis(tri-tert-butylphosphine)palladium (70.0 mg) at 0° C., and the mixture was stirred for 1 hr under an argon atmosphere while heating to 80° C. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio) to give the title compound (0.56 g, 46%) as a colorless oil.

Provenance & Evidence