Diethyl Ether → 1-(2-Chloropyridin-4-yl)ethan-1-one

Participants

Reaction Steps

To a solution of 2-chloro-4-cyanopyridine (41.6 g) in dry ether under a nitrogen-atmosphere was added methylmagnesium iodide (200 mL, 3M in ether) dropwise. The resulting mixture was stirred at room temperature overnight. The solids which were formed were collected and poured immediately on a mixture of 1000 g ice, 500 mL water and 250 mL 6N HCl. The aqueous solution was allowed to reach room temperature and then extracted with ether (800 mL) and the combined organic layers were dried (sodium sulfate) and evaporated to give a red oil which crystallised on standing. This material was taken up in a mixture of ether (ca 300 mL) and heptane (˜50 mL). The solution was cooled in an acetone/dry-ice bath which resulted in formation of yellow solids that were filtered and air-dried for 30 minutes to give the title compound (21.7 g) as a yellow solid.

Provenance & Evidence