Chlorotrimethylsilane → 2-Trimethylsilylthiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 8.28 g of 2-bromothiazole in 100 ml of ether at -78° C., under argon, was added 21.7 ml of n-butyl lithium in hexane. The mixture was stirred at -78° C. for 45 minutes then 6.8 ml of trimethylsilyl chloride was added. This mixture was stirred at -78° C. for 1 hour, warmed to -30° C. over 1 hour, then 0° C. over 1/2 hour and kept at 0° C. for 1 hour. The reaction was quenched with 50 ml of 50% saturated sodium bicarbonate and then diluted with 50 ml of ether. The ether solution was washed with 50 ml of brine, dried, filtered and evaporated, giving 10.81 g of 2-trimethylsilylthiazole as an amber colored oil.

Provenance & Evidence