Diethyl Ether → HCID 66915011, compound

Participants

Reaction Steps

A solution of ethyl (3-(2-thienyl)prop-2-enoate (2.50 g, 13.70 mmol) and toluenesulfonylmethyl isocyanide (2.90 g, 14.90 mmol) in dimethylsulfoxide:diethyl ether (12.50 mL:20 mL) was added drop wise over a period of 15 min to a stirred solution of 60% sodium hydride in mineral oil (760 mg, 18.30 mmol) in diethyl ether (20 mL) at 10° C. Stirring was continued for 3 h at room temperature and the reaction mixture was quenched with saturated ammonium chloride solution and extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude compound which was purified by column chromatography over silica gel (100-200 mesh) using 18% ethyl acetate in pet ether as eluent to afford 4-thiophene-2-yl-1H-pyrrole-3-carboxylic acid ethyl ester (100 mg, 42%) as a solid.

Provenance & Evidence