6-Methoxy-2-pyridinecarboxaldehyde → 2-Methoxy-6-vinylpyridine

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl(triphenyl)phosphonium bromide (7.07 g, 19.8 mmol, 1.1 eq) in dry THF (50 ml) at 0° C. is added n-butyl lithium (1.6M in cyclohexane, 12.5 ml, 19.8 mmol, 1.1 eq). After stirring at 0° C. for 20 minutes, a solution of 6-methoxypyridine-2-carbaldehyde a1-50 (2.5 g, 18 mmol, 1 eq) in dry THF (10 ml) is added dropwise to the mixture. The reaction mixture is warmed to room temperature for 30 minutes. The reaction mixture is quenched with 3 drops of water, and Rochelle salt is added (10 g). The mixture is filtered on Celite and MgSO4. The crude residue is distilled to afford 400 mg of pure 2-ethenyl-6-methoxypyridine a1-51.

Provenance & Evidence