Acetic Acid → Ethyl 3-phenyl-2-(thiophene-2-carbonyl)acrylate

Participants

Reaction Steps

A solution of ethyl 3-oxo-3-(thiophen-2-yl)propanoate (4.10 g, 20.7 mmol), benaldehyde (2.32 ml, 22.8 mmol), piperidine (0.205 ml, 2.07 mmol) and acetic acid (0.593 ml, 10.4 mmol) in benzene (80 ml) was heated at 85° C. for 5 hours using a Dean-Stark trap for removal of the water formed. The reaction solution was concentrated. The resulting residue was purified via flash chromatography (silica gel cartridge with eluent of 0-5% ethyl acetate/hexane) to give ethyl 3-phenyl-2-(thiophene-2-carbonyl)acrylate as a white solid (5.563 g, 94% yield). LCMS m/z 309.1 (M+23); HPLC: Rt 3.15 min.

Provenance & Evidence