Methanol → 4H,5H,6H-thieno[2,3-c]pyrrol-6-one

Participants

Reaction Steps

A mixture of methyl 3-(aminomethyl)thiophene-2-carboxylate (4.5 g, 26.3 mmol) and K2CO3 (3.64 g, 26.3 mmol) in 1:1 MeOH:EtOH (600 mL) was heated overnight under reflux. The reaction was concentrated and purified by flash chromatography over silica gel (50-100% EtOAc/hexane) to yield 4H-thieno[2,3-c]pyrrol-6(5H)-one (2.2 g, 60% yield) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.87 (d, J=4.8 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 4.39 (s, 2H); MS (EI) m/z=140.2 [M+1]+.

Provenance & Evidence