Acetic Anhydride → (4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

The 4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-2,3,5-trimethylpyridine 1-oxide (5.06 g, 18 mmol) obtained in the step (11e) was mixed with acetic anhydride (50 ml, 529 mmol) and the mixture was stirred at 85° C. for 1.5 hours. After cooled to room temperature, the reaction mixture was concentrated. Methanol (50 ml) and a 5N aqueous sodium hydroxide solution (50 ml, 250 mmol) were added to the residue and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue was separated between water and ethyl acetate. The organic layer was washed with a 1N aqueous sodium hydroxide solution twice and dried over anhydrous magnesium sulfate, filtered and concentrated to obtain the title compound (3.02 g, yield: 59.6%) as a brown oil.

Provenance & Evidence