Tributyltin Chloride → 5-(Tributylstannyl)-1,3-thiazole

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.6M, 4.95 mL, 7.88 mmol) was added to a solution of 2-trimethylsilylthiazole (826 mg, 5.25 mmol) in anhydrous ether (45 mL) stirred at −78° C. under nitrogen. After 20 min, tri-n-butylstannyl chloride (2.57 g, 7.88 mmol) was added, then the solution was allowed to warm to room temperature, and stirred for another 1 h. The mixture was quenched and washed with 1N sodium hydroxide, dried through MgSO4, and then the solvent was evaporated to give a brown oily residue. The residue of 2-trimethylsilyl-5-tributylstannyl-thiazole was passed through a column of neutral alumina eluting with a gradient of ammoniated methanol in chloroform to give the sub-title compound as a yellow oil (1.5 g).

Provenance & Evidence