Tributyltin Chloride → 4-(Tri-n-butylstannyl)thiazole

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.6M, 3.1 mL, 4.94 mmol) was added to a solution of 2,4-dibromothiazole (1 g, 4.12 mmol) in anhydrous ether (25 mL) stirred at −78° C. under nitrogen. After 15 min, chlorotrimethylsilane (493 mg, 4.53 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 (905 mg). The residue was purified by the distillation to give 4-bromo-2-trimethylsilylthiazole (650 mg) as a light-brown oil. Under nitrogen, the 4-bromo-2-trimethylsilylthiazole (340 mg, 1.44 mmol) was then dissolved in anhydrous ether (15 mL), and the resulting solution was stirred at −78° C. n-Butyllithium (1.5M, 1.4 mL, 2.16 mmol) was added, and the resulting solution was stirred at −78° C. for 30 minutes. Tri-n-butylstannyl chloride (703 mg, 2.16 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-4-tri-n-butylstannylthiazole was passed through a column of neutral alumina eluting with a gradient of ammoniated methanol in chloroform to give the sub-title compound, 4-tri-n-butylstannylthiazole as a yellow oil (330 mg).

Provenance & Evidence