2-Methoxy-4,6-dimethylnicotinaldehyde → 2-Methoxy-4,6-dimethyl-3-vinylpyridine

Participants

Reaction Steps

Potassium tert-butoxide (1.63 g, 14.54 mmol) is added to a suspension of methyl triphenylphosphine (5.20 g, 14.54 mmol) in toluene (70 mL) and the mixture is stirred at room temperature of 0.5 hr. To this yellow-orange mixture is added a solution of 4,6-dimethyl-2-methoxypyridine-3-carbaldehyde (1.20 g, 7.27 mmol) in toluene (10 mL). After 1.5 hr. the reaction mixture is washed with water (150 mL), with brine (150 mL), dried, filtered and concentrated and the residue is purified by chromatography eluting with cyclohexane-5% ethyl acetate. Product containing fractions are combined and concentrated to afford 2-methoxy-4,6-dimethyl-3-vinylpyridine (0.66 g, 55.5% yield) as an oil containing triphenylphosphine oxide.

Provenance & Evidence