Trimethyltin chloride → 2-Methyl-5-(trimethylstannyl)thiazole

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of 2-methylthiazole (1.0 g, 10 mmol) in anhydrous diethyl ether (20 mL) under an atmosphere of nitrogen was added n-butyllithium (2.5M solution in hexanes, 5.2 mL, 13 mmol) dropwise over 10 minutes. The reaction mixture was stirred for 1 h and then allowed to warm to 0° C. and stirred for 1 h. The reaction mixture was then cooled to −78° C. and a solution of chlorotrimethylstannane (1.8 g, 9.0 mmol) in anhydrous diethyl ether (10 mL) was added dropwise over 10 minutes. The reaction mixture was stirred for 30 minutes and then allowed to warm to room temperature and stirred for 16 h. The reaction was quenched with water (20 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered, and evaporated in vacuo to afford the title compound as a yellow oil which was used without any further purification.

Provenance & Evidence