Diethyl Ether → 1-(6-Chloropyridin-3-yl)propan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-N-methoxy-N-methyl nicotinamide (6.0 g, 30 mmol) (produced as disclosed in Perner, R. J. J. Med. Chem. 2003, 46, 5249) in THF (100 mL) was added a 3M solution of ethyl magnesium chloride in ether (15 mL, 45 mmol). The reaction mixture was heated under reflux for 4 hours and then stirred at approximately 25° C. for 14 hours. The reaction mixture was treated with a saturated aqueous solution of ammonium chloride (100 mL) and then extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by chromatography over silica gel, eluting with 10 percent ethyl acetate in hexane to give product as a white solid. (2.8 g, 60 percent yield).

Provenance & Evidence