Acetic Anhydride → (5-Bromo-4-isobutoxypyridin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-4-isobutoxy-2-methylpyridine 1-oxide (3.40 g) and acetic anhydride (50 mL) was stirred at 80° C. for 1 hr. The solvent in the reaction mixture was evaporated under reduced pressure, and the residue was dissolved in THF (50 mL) and methanol (25 mL). 1N Aqueous sodium hydroxide solution (50 mL) was added to the obtained solution, and the reaction mixture was stirred at room temperature for 15 min. 1N Hydrochloric acid (50 mL) was added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.20 g) as a pale-yellow oil.

Provenance & Evidence