Triethylamine → HCID 11645580, compound

Participants

Reaction Steps

To a solution of (3-(4-dimethylamino-phenylsulfanyl)-phenyl)-methanol (255 mg, 0.98 mmol) and triethylamine (1.3 mL, 9.2 mmol) in dimethyl sulfoxide (5 mL) was added a solution of pyridine-sulphur trioxide (469 mg, 2.95 mmol) in dimethyl sulfoxide (5 mL). The mixture was stirred for 1 hour at room temperature and water (20 mL) and ethyl acetate (40 mL) were added. The organic layer was washed with water (3×10 mL) and brine (20 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a colourless oil. This oil was dissolved in dichloromethane (10 mL) and (triphenylphosphoranylidene)-acetic acid ethyl ester (700 mg, 2.0 mmol) was added. The mixture was stirred at reflux for 3 hours and concentrated under reduced pressure. The residue was purified by flash chromatography (20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine) to give the title compound as a colourless oil (240 mg, 74%).

Provenance & Evidence