Acetone → HCID 19879231, compound

Participants

Reaction Steps

A solution of 5 g (17 mmoles) of 2-(4-mercaptophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]-imidazole in dry tetrahydrofuran is treated at -20° C. with a solution of 17 mmoles of lithium diethylamide from 6.8 ml of 2.5 M n butyl lithium. After warming, a solution of 1.57 g (17 mmoles) of trimethylsilylmethylchloride in tetrahydrofuran is added dropwise. When the reaction is complete, the mixture is immersed in an ice bath and a second solution (17 mmoles) of lithium diethylamide is added. After stirring for 15 minutes, a solution of 0.99 g (17 mmoles) of acetone in tetrahydrofuran is added, and the mixture is stirred 15 minutes at 0° and 15 minutes at 25° C. The mixture is poured into water, extracted with methylene chloride, and the organic layer dried, and chromatographed on silica to afford the desired titled compound.

Provenance & Evidence