Ammonium Chloride → HCID 131735871, compound

Participants

Reaction Steps

To a solution of 3,3-dimethoxybutan-2-one oxime (270 mg) in tetrahydrofuran (2.7 ml) was added dropwise, at 0° C. under argon, n-butyllithium (2M in tetrahydrofuran, 1.83 ml). After stirring for a further 5 minutes, a solution of 2-{[3-(trimethylsilyl)prop-2-yn-1-yl]oxy}benzaldehyde (232 mg) in tetrahydrofuran (1 ml) was added dropwise to the reaction mixture, which was stirred for a further 1 hour. Subsequently, concentrated ammonium chloride solution was added to the reaction mixture, and the aqueous phase was removed and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. Purification by column chromatography gave 1-hydroxyl-4,4-dimethoxy-1-(2-{[3-(trimethylsilyl)prop-2-yn-1-yl]oxy}phenyl)pentan-3-one oxime (482 mg, 69%).

Provenance & Evidence