Thionyl Chloride → 3-[Chloro(cyclohexyl)methyl]-2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophene

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclohexyl{2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}methanol (2.29 g) synthesized in Example 69 (7) in toluene (25 mL) was added thionyl chloride (907 μL), and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was cooled to 0° C., saturated aqueous sodium hydrogen carbonate 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=1:4, volume ratio) to give the title compound (2.08 g, 86%) as a pale-brown solid.

Provenance & Evidence