Trifluoroacetic acid → 5-Cyclohexyl-2,3-bis(4-methoxyphenyl)thiophene

Participants

Reaction Steps

A solution of 1-[4,5-bis(4-methoxyphenyl)thien-2-yl]cyclohexanol (5.8 g, 14.7 mmole) in 125 ml of methylene chloride at 0° was treated sequentially with triethylsilane (4.7 ml, 2 equiv.) and trifluoroacetic acid (1.3 ml, 1.14 equiv.). The reaction mixture was stirred for 40 minutes at 0° and for 2 hours at room temperature, and then partitioned between methylene chloride and water. The organic phase was washed with saturated aqueous sodium bicarbonate and brine, dried and concentrated in vacuo. Recrystallization from ethanol provided the title compound (3.9 g, 70%), m.p. 95°-98°. Proton NMR and infrared (IR) spectra were consistent with the assigned structure. MS: m/z 378 (M+).

Provenance & Evidence