5-Phenoxypyridine-2-carboxylic acid → Benzyl 3-oxo-3-(5-phenoxypyridin-2-yl)propanoate

Participants

Reaction Steps

To a solution of 5-phenoxypyridine-2-carboxylic acid (10 g, 46.5 mmol) in tetrahydrofuran (150 ml) was added N,N′-carbonyldiimidazole (8.29. g, 51.1 mmol), and the mixture was heated under reflux for 1 hr. After cooling the reaction solution to room temperature, monobenzyl malonate magnesium salt (10.5 g, 25.6 mmol) was added, and the mixture was heated under reflux for 2 hrs. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the objective substance (11.2 g, 76%).

Provenance & Evidence