Ethanolamine → 1,2-Dimethyl-4-phenyl-1H-pyrrole

Participants

Reaction Conditions

Reaction Steps

A suspension of 1,5-dimethyl-3-phenyl-pyrrole-2,4-dicarboxylic acid (60 g, 0.23 mol) and 2-aminoethanol (300 mL) was heated to 175° C. under a nitrogen atmosphere for 30 min. The mixture was allowed to cool to room temperature, diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed successively with water (3×100 mL) and brine (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo at a temperature below 40° C. to afford the crude product. Flash column chromatography over neutral alumina using 5% ethyl acetate in petroleum ether as eluent afforded 1,2-dimethyl-4-phenyl-pyrrole (30.5 g, 78%) as a white solid.

Provenance & Evidence