Ammonium Chloride → [6-(Dimethoxymethyl)-2-methoxypyridin-3-yl]methanol

Participants

Reaction Steps

Diisopropylethylamine (4.56 mL) and Bop reagent (registered trademark) (10 g) were added to a solution of 6-(dimethoxymethyl)-2-methoxypyridine-3-carboxylic acid (4.1 g) in tetrahydrofuran (40 mL) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was cooled to 0° C. and sodium borohydride (2.72 g) was added, followed by stirring at room temperature overnight. The reaction solution was poured into a saturated ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→1:1) to give [6-(dimethoxymethyl)-2-methoxypyridin-3-yl]methanol (2.3 g, 60%) as a colorless oil.

Provenance & Evidence