N-Methoxy-N-methylacetamide → HCID 59463280, compound

Participants

Reaction Steps

To a solution of 3-bromo-5-{[(4-methoxybenzyl)oxy]methyl}pyridine (4.4 mmol) in methyl t-butyl ether (20 mL) was added n-BuLi (2.5M in hexane, 1.96 mL) dropwise at −78° C. The reaction mixture was allowed to stir for 15 min and then N-methoxy-N-methylacetamide (6.7 mmol) in methyl t-butyl ether (3 mL) was added dropwise. The reaction mixture was allowed to stir for 30 min at −78° C. and then diluted with water and allowed to warm to rt. After stirring for 30 min, the phases were separated and the aqueous solution was extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 1-(5-{[(4-methoxybenzyl)oxy]methyl}pyridin-3-yl)ethanone (3.1 mmol, 70%) as a white solid. LCMS: (FA) ES+ 272.1.

Provenance & Evidence