Tetrahydrofuran → 1-(6-Chloropyridin-2-yl)ethanone

Reaction equation

[Cl:1][C:2]1[CH:7]=CC=C(C#N)[N:3]=1.[CH3:10][Mg]I.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:15][CH:14]=[C:13]([C:17](=[O:16])[CH3:10])[N:3]=1

Participants

Procedure

A solution of 2-chloro-6-cyanopyridine (50 g) in THF (400 ml) is cooled to −5° C. and a solution of methylmagnesium iodide in diethyl ether (3 M, 200 ml) is added. After 1 h at 0° C. the ether is destilled off and the THF-mixture is heated to 60° C. for 1 h. The THF is evaporated and the residue is treated with ice water and acidified with 2 M hydrochloric acid. The water phase is extracted with dichloromethane and after drying and evaporation of the organic phase, the residue is purified by silica-gel flash chromatography. The title compound is obtained as an oil (11.2 g).