Tributyltin Chloride → HCID 22631437, compound

Participants

Reaction Steps

Tri-n-butylstannyl chloride (3.53 ml) and 12.34 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added to a solution of 2.32 g of 7-(2-azidoethyl)thioimidazo[5,1-b]thiazole in 75 ml of THF at −65° C. under an argon atmosphere. The temperature of the mixture was raised to −30° C. over a period of 2 hr, during which time a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (1.0 ml) was added to the mixture four times. An aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, followed by washing with brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to prepare 4.62 g of the title compound.

Provenance & Evidence