5-[5-(4-Chloro-phenyl)-2-ethyl-thiophen-3-yl]-4-hydroxy-cyclopent-2-enone → 2-[5-(4-Chloro-phenyl)-2-ethyl-thiophen-3-yl]-cyclopent-4-ene-1,3-dione

Participants

Reaction Steps

To a solution of 5-[5-(4-chloro-phenyl)-2-ethyl-thiophen-3-yl]-4-hydroxy-cyclopent-2-enone (300 mg, 0.95 mmol) in acetone (5 ml) at 0° C. is added, dropwise, Jones' reagent and the resulting yellow solution stirred at 0° C. for 80 minutes. Reaction is quenched by the addition of propan-2-ol (1 ml) and stirred for a further 2 hours. Brine (50 ml) is added and the reaction is extracted with ethyl acetate (2×50 ml). The combined organics are then washed with brine, dried over magnesium sulphate and concentrated in vacuo to give 2-[5-(4-chloro-phenyl)-2-ethyl-thiophen-3-yl]-cyclopent-4-ene-1,3-dione as an orange solid (248 mg).

Provenance & Evidence