Methoxymethyl-triphenylphosphonium chloride → HCID 86670916, compound

Participants

Reaction Steps

To a suspension of (methoxymethyl)triphenylphosphonium chloride (34.5 g, 100.6 mmol) in THF (500 mL) at −10° C. was added LDA (60 mL, 2 mol/L). The mixture was stirred at −10° C. for 1 hour before addition of 6-bromopicolinaldehyde (10 g, 53.8 mmol) in THF (200 mL). The reaction mixture was then allowed to warm to room temperature and stirred at room temperature for 12 hours. The solution was then partitioned between water and ether. The aqueous fraction was separated and extracted twice with ether. The organic layers were washed with brine and dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give the crude product which was purified by chromatography (petroleum ether:ethyl acetate, 20:1) to give 2-bromo-6-(-2-methoxy-vinyl)-pyridine. (Yield 9.3 g, 80%). LC-MS: [M+H]+ 215.

Provenance & Evidence