Triethylamine → 3-Methyl-4'-trifluoromethyl-biphenyl-4-carbaldehyde

Participants

Reaction Steps

A solution of (3-methyl-4′-trifluoromethyl-biphenyl-4-yl)-methanol (1.613 g, 6.060 mmol) in dimethylsulfoxide (DMSO, 12.0 mL) is treated with Et3N (5.50 mL, 39.460 mmol) and pyridine-sulfur trioxide (2.902 g, 18.235 mmol) in a cold water bath. The bath is removed after 3 min. and the reaction is stirred overnight. The reaction mixture is poured into H2O (50 mL) and extracted with EtOAc (3×50 mL). Combined organic extracts are dried over MgSO4, filtered, and conc. The residue is loaded onto silica gel and eluted with hexanes using a gradient from 5% EtOAc to 33% EtOAc to provide 3-methyl-4′-trifluoromethyl-biphenyl-4-carbaldehyde (1.221 g, 76%) as white crystals.

Provenance & Evidence