Sodium Hydroxide → HCID 68858921, compound

Participants

Reaction Steps

Solid 3-chloroperbenzoic acid (60 percent, 18.1 g, 68.6 mmol) was added in portions over 1 hour to a chilled (6° C.) solution of 5-difluoromethoxy-3-methyl-2-methylsulfanylpyridine (6.4 g, 31.2 mmol) in methylene chloride (200 mL). The reaction was stirred overnight while warming to room temperature. Aqueous 1N sodium hydroxide (65 mL) was added in portions, raising the pH to ca. 6. Saturated aq. sodium bicarbonate (60 mL) was added, raising the pH of the aqueous phase to ca. 8. Aqueous 10 percent sodium sulfite was added, and after stirring for 10 minutes, the layers were separated. The aqueous layer was extracted with methylene chloride (50 mL) and the organic layers were combined, washed with brine, and dried (Na2SO4). Filtration and removal of solvent left a clear oil, 8 g, that was purified by chromatography on silica, eluting with 1.5 vol percent acetonitrile in methylene chloride to give product, 6.3 g, 26.6 mmol, 85 percent yield.

Provenance & Evidence