3-Pyridinecarboxaldehyde → HCID 54529674, compound

Participants

Reaction Conditions

Reaction Steps

Phenyllithium (111 ml of 1.8M solution in ether) was added dropwise to a stirred suspension of (methoxymethyl) triphenylphosphonium chloride (68.6 g) in dry ether (600 ml) at -50° C. The mixture was stirred at -50° C. for 2 hours and then allowed to reach 0° C. over 30 minutes. 3-Pyridinecarboxaldehyde (10.70 g) was added dropwise with stirring, and the mixture was stirred at room temperature for 18 hours. Anexcess of ammonium chloride solution was then added and the layers were separated. The aqueous layer was separated and washed with ether, and the organic layers were combined and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel initially using ethyl acetate/hexane (1:4) as eluant. The polarity was gradually increased to ethyl acetate/hexane (1:1) to give the pure product as an oil(8.82 g) which was used directly in the next stage.

Provenance & Evidence