Reaktion #511574

Reaktionsgleichung

ethyl 3-phenyl-2-(thiophene-2-carbonyl)acrylate

aluminum trichloride

→

ethyl 6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate

Lösungsmittel

nitroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic phase was washed with brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give a brown oil
6. 6
   SonstigeThe crude product was purified via flash chromatography 9 (silica gel cartridge with eluent of 0-15% ethyl acetate/hexane)

Vorschrift

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.

Quelle