Diethyl Ether → HCID 86714641, compound

Participants

Reaction Conditions

Reaction Steps

5-Acetyl-1-benzylimidazole (24.97 mmol, 5 g) was dissolved in dry diethyl ether (100 ml) under nitrogen atmosphere. The mixture was cooled to −75° C. and lithium bis(trimethylsilyl)amide (27.5 mmol, 27.5 ml) was added dropwise. The resulting mixture was stirred at −75° C. for an hour. Diethyl oxalate (32.5 mmol, 4.74 g) was added and the mixture was allowed to warm to ambient temperature after which the mixture was stirred for a day at RT. The formed precipitate was removed by filtration and the precipitate was washed with diethyl ether. The precipitate was dried under vacuum. 7.38 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.22 (t, 3H), 4.11 (q, 2H), 5.61 (s, 2H), 6.17 (s, 1H), 7.15-7.31 (m, 5H), 7.48 (d, 1H), 7.88 (d, 1H).

Provenance & Evidence