Sodium Hydroxide → 4-formyl-[(2-propynyl)]-1H-pyrrole-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.36 g of aluminium chloride in 6 ml of anhydrous methylene chloride was cooled to -78° C. and 1.3 g of the product of Step A in solution in 8 ml of methylene chloride and 0.5 ml of nitromethane were added. 1.49 g of dichloromethyl ether in solution in 15 ml of methylene chloride were added at -55° C. and the reaction mixture was kept for 1 hour at -60° C., then allowed to return to 20° C., at which temperature it was held for 18 hours. It was poured into water, stirred, and neutralized to pH 7 by addition of 33 ml of 2N sodium hydroxide. Extraction was with methylene chloride and the extracts were washed with a 1M potassium bicarbonate solution, dried and concentrated to dryness to obtain 1.5 g of 4-formyl-[(2-propynyl)]-1H-pyrrole-2-carbonitrile which was washed with dupentane and dried to obtain 1.1 g of the said product melting at 97° C.

Provenance & Evidence