Diethyl Ether → Di-4-pyridinylmethanone

Participants

Reaction Conditions

Reaction Steps

To a solution of n-butyllithium (2.5 M, 39 mL, 0.096 mol) in 300 mL of ether cooled to -75° C. was added 4-bromopyridine (15.1 g, 0.095 mol) in 100 mL of ether at such a rate to maintain the internal temperature below -50° C. The resulting mixture was stirred at -75° C. for 15 min, and N-methyl,N-methoxyurethane (5.8 g, 0.043 mol) in 25 mL of ether was added over a 20 min period, and the mixture was warmed to room temperature and then stirred for 2 h. The mixture was quenched with 300 mL of water and the layers were separated. The organic layer was extracted with 6 N HCl solution, and the aqueous layer was basified with 10% NaOH solution. The basic solution was extracted with chloroform, the organic layer dried over sodium sulfate, concentrated in vacuo, and purified by chromatography on silica (ethyl acetate) to afford 3.9 g (48.7%) of di-(4-pyridyl)ketone.

Provenance & Evidence