Thionyl Chloride → 4H,5H,6H-cyclopenta[b]thiophen-4-one

Participants

Reaction Steps

To a solution of 3-thiophene-2-yl-propionic acid (Intermediate AC) (1.75 g, 0.01122 mol) in dichloromethane (50 mL) was added SOCl2 (1.67 mL, 0.02244 mol) and stirred at room temperature for 6 h. This solution was added dropwise to a suspension of AlCl3 (2.98 g, 0.02244 mol) in dichloromethane (50 mL) over 45 minutes. The resulting mixture was stirred at room temperature for 12 h. The system was quenched by dropwise addition of water (10 mL) and extracted with dichloromethane. The organics were dried with MgSO4 and the solvent was removed in vacuo. The title compound was purified by silica gel column chromatography using 4:1 Hexanes:ethyl acetate as the eluent. MS m/z 139.1 (M+H)+;

Provenance & Evidence