Hexane → HCID 23260319, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of methoxymethyltriphenyl phosphonium chloride (12.48 g) in tetrahydrofuran (60 ml) under argon was cooled in an ice-bath. Potassium tert-butoxide (36.41 ml, 1M solution in tetrahydrofuran) was then added dropwise over 30 minutes to give a deep orange-red colour. Stirring was continued at 0-5° C. for 50 minutes then the mixture was cooled to −78° C. 2-Pyridinecarboxaldehyde was added dropwise and stirring continued at −78° C. for a further 2 h then allowed to warm to room temperature and stirred for 2 h. Hexane (100 ml) was added, the mixture filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting, with 10% ethyl acetate in hexane to give the pure cis-2-(2-methoxyvinyl)pyridine (0.91 g, 24%):

Provenance & Evidence