Acetic Anhydride → HCID 13654799, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,3-dimethyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine-1-oxide (2.6 g) in acetic anhydride (8 ml), concentrated sulfuric acid (2 drops) was added; and the solution was stirred at 110° C. for 4 hours and then concentrated. The resulting residue was dissolved in methanol (20 ml) and a solution of sodium hydroxide (1.2 g) in water (5 ml) was added, after which the mixture was stirred at room temperature for 30 minutes. After concentration, water was added, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and the solvent was evaporated, after which the resulting residue was applied on a silica gel (50 g) column, eluted with chloroform-methanol (10:1) and then recrystallized from isopropyl ether to give 1.6 g of 2-hydroxymethyl-3-methyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine as yellow crystals (melting points: 67°~68° C.).

Provenance & Evidence