Aluminum(III) Chloride → ethyl 6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate

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Reaction Steps

A solution of ethyl 3-phenyl-2-(thiophene-2-carbonyl)acrylate (3.118 g, 10.9 mmol) and aluminum trichloride (1.725 g, 13 mmol) in nitroethane (50 ml) was heated at 75° C. for 3 hours. The reaction mixture was poured into 1N HCl-ice solution, and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and concentrated to give a brown oil. The crude product was purified via flash chromatography 9 (silica gel cartridge with eluent of 0-15% ethyl acetate/hexane) to give ethyl 6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate as am amble liquid, 3.12 g, quantitative yield. HPLC: Rt 2.873, 3.188 min.

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