Hydrochloric Acid → Methyl 3-benzyloxypicolinate

Participants

Reaction Steps

Methyl 3-hydroxypicolinate (2.0 g) was dissolved in 100 ml of acetone. Potassium carbonate (3.4 g) and 3.4 ml of benzyl bromide were added to the solution, and a reaction was allowed to proceed at room temperature overnight. The reaction solution was then refluxed for 4 hr. Water (50 ml) was added thereto, and the mixture was neutralized with 1 N hydrochloric acid, followed by concentration under the reduced pressure. Methylene chloride and water were added to the residue. The organic layer was dried over magnesium sulfate, and was then dried under the reduced pressure. The dried organic layer was then purified by column chromatography (chloroform-methanol) to give 2.1 g (yield 62%) of methyl 3-benzyloxypicolinate.

Provenance & Evidence