4-Acetylpyridine → 4-(2-Methyloxiran-2-yl)pyridine

Participants

Reaction Steps

Sodium hydride (5.0 g of a 50% dispersion in oil) was added portionwise to a stirred suspension of trimethylsulphoxonium iodide (22.0 g) in THF (150 cm3) and the mixture was heated under reflux for 3 hours. After cooling to 40°, 4-acetyl-pyridine (10.0 g) was added and the mixture was again heated under reflux for 1 hour. The cooled mixture was evaporated in vacuo, partitioned between ether (100 cm3) and water (50 cm3) and the aqueous phase was further extracted with ether (2×50 cm3). The combined dried extracts were evaporated to afford 2-methyl-2-[4-pyridyl]oxirane as a crude oil.

Provenance & Evidence