3-Pyridinecarboxaldehyde → HCID 13590429, compound

Participants

Reaction Conditions

Reaction Steps

10.11 g (50.9 mmol) of 4-chloromethylbenzaldehyde ethylene acetal and 8.46 g (50.9 mmol) of triethyl phosphite were heated without solvent, with magnetic stirring, at an oil bath temperature of 200°-210° C. until gas evolution was complete (about 1 h). After cooling, 70 ml of dimethylformamide (filtered through basic alumina, activity I) and 5.5 g (102.0 mmol) of sodium methylate were added. The mixture was cooled to 5° C. and, with magnetic stirring and cooling, a solution of 5.45 g (50.9 mmol) of pyridine-3-aldehyde in 20 ml of dimethylformamide was added dropwise within 15 min (during which the temperature rose to 25° C.), and the mixture was then stirred at room temperature for 1 h. The reaction mixture was diluted with 250 ml of toluene and washed twice with water. The combined wash phases were extracted twice with toluene. Drying of the combined organic phases over magnesium sulfate and removal of the solvent in vacuo provided 10.94 g of a yellowish solid. Recrystallization from cyclohexane produced 8.74 g, and working up of the mother liquor produced a further 0.60 g.

Provenance & Evidence