m-Chloroperbenzoic acid → 3-Benzyloxy-2-hydroxymethyl-4-methoxypyridine

Participants

Reaction Conditions

Reaction Steps

3-Benzyloxy-4-methoxy-2-methylpyridine (23.0 g) was dissolved in 200 ml of dichloromethane. m-Chloroperbenzoic acid (20.7 g) was added to the solution under ice cooling, and a reaction was allowed to proceed at room temperature overnight. The reaction product was washed with an aqueous saturated sodium hydrogensulfite solution and an aqueous saturated sodium hydrogencarbonate solution, and the washed reaction product was dried over anhydrous sodium sulfate. The solvent was concentrated under the reduced pressure. Acetic anhydride (200 ml) was added to 35.5 g of the concentrate as a light yellow oil, and a reaction was allowed to proceed at 100° C. for one hr. Ethanol (100 ml) was then added thereto, and the mixture was further refluxed for one hr. The reaction solution was concentrated under the reduced pressure. A 2 M solution (200 ml) of sodium hydroxide in 50% methanol was added to the concentrate, and the mixture was stirred at 80° C. for one hr. The reaction solution was concentrated under the reduced pressure. The concentrate was extracted with chloroform. The extract was washed with saturated brine, and was then dried over anhydrous sodium sulfate, followed by concentration under the reduced pressure to give 19.6 g (yield 80%) of 3-benzyloxy-2-hydroxymethyl-4-methoxypyridine as a yellowish brown solid.

Provenance & Evidence