Diethyl Ether → Methyl 2-formylisonicotinate

Participants

Reaction Steps

1.07 g of dimethyl pyridine-2,4-dicarboxylate was dissolved in 20 ml of toluene, and with stirring under cooling at -80° to -70° C., 6.04 ml of a 1M toluene solution of diisobutylaluminium hydride was added dropwise over 2.5 hours, and the mixture was stirred at this temperature for 1 hour. The reaction mixture was poured into ice water, and ethyl ether was added. The organic layer was separated, worked up in a customary manner, and then purified by medium-pressure liquid chromatography Lobar column, size B, Lichroprep Si 60 (E. Merck Co.); eluting solvent: hexane/ethyl acetate=4/1→3/1) to give 0.27 g (yield 30%) of methyl 2-formylisonicotinate as a colorless crystalline powder.

Provenance & Evidence