Tetrabutylammonium Fluoride → HCID 15053160, compound

Participants

Reaction Steps

To a solution of 8-(2-benzimidazolyl)thiomethyl-1-(3-trimethylsilyl-2-propinyl)-1,2,3,4-tetrahydroquinoline (400 mg) in tetrahydrofuran (20 ml) was added 1M solution of tetra-n-butylammonium fluoride with stirring under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. After distilling off the solvent, the resulting residue was extracted with dichloromethane. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (5.5:1)], and recrystallized from dichloromethane-diethyl ether to give 8-(2-benzimidazolyl)thiomethyl-1-propargyl-1,2,3,4-tetrahydroquinoline (0.35 g).

Provenance & Evidence