Methanol → 2-(1-Oxo-1lambda~5~-pyridin-2-yl)-1-phenylethan-1-one

Participants

Reaction Steps

A solution of 2-picoline N-oxide (4.4 g, 0.04 mol) in benzene (25 ml) was added to a suspension of sodium hydride (3.2 g of 60% oil dispersion) and methyl benzoate (9.94 ml, 0.08 mol) in dry benzene (100 ml). The reaction mixture was refluxed overnight. Methanol (15 ml) was added to the cooled reaction mixture, followed by water (150 ml). The aqueous layer was separated and extracted with chloroform (2×40 ml). The aqueous layer was acidified with 1N HCl and extracted with chloroform. The combined organic layers were dried (MgSO4) and concentrated to give the subtitle ketone as a solid (7 g), mp 146°-148° C.

Provenance & Evidence