Acetic Anhydride → (6-Cyano-5-methyl-2-pyridinyl)methyl acetate

Participants

Reaction Steps

To acetic anhydride (20 ml) at 120° was added 3,6-dimethyl-2-pyridine-carbonitrile 1-oxide (5.28 g) and the solution heated at 120° for 5 minutes then under reflux for 2 hours. After cooling the solution was added to ice (ca. 150 g) and the mixture neutralized with sodium bicarbonate. It was extracted with ether (170 ml then 2×75 ml) and the combined extracts washed with brine (60 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by Biotage chromatography eluting with 2:1 hexane:ethyl acetate to afford the title compound (3.62 g, 67%) as a pale yellow oil

Provenance & Evidence