Water → 4-Methoxy-2,6-dimethylpyridine

Participants

Reaction Steps

Sodium methoxide (2 eq.) was dissolved in methanol (1.5 volumes) and dry dimethylformamide (2 volumes). The solution was heated to (95-100ℑ C.)and while stirring under a stream of nitrogen, 4-chlorolutidine (1 eq.) was added dropwise. At the end of the reaction (about 2 hours), the mixture was cooled in an ice bath and cold water (10 volumes) was added. The product was extracted with dichloromethane (3×2 volumes). The combined organic extracts were dried over sodium sulfate, filtered and the solvent was evaporated under vacuum. Light yellow oil was obtained in 72% yield.

Provenance & Evidence