N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine → 5-((E)-3-Dimethylamino-acryloyl)-1H-pyrrole-3-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-Acetyl-1H-pyrrole-3-carboxylic acid ethyl ester (0.560 g, 3.1 mmol) in 5 mL of dimethylformamide, N,N-dimethylformamide diisopropyl acetal (1.9 mL, 9.3 mmol) was added. The mixture was stirred for at 65° C. for 6 hrs. After cooling to room temperature an aqueous solution of NaHCO3 2% (30 mL) was added and extracted with ethyl acetate (50 mL×2). Organic layer was separated and washed with water (10 mL) and brine (10 mL), dried over sodium sulfate, filtered, and concentered in vacuo to give 0.531 g (72%) of the title compound.

Provenance & Evidence