Chlorotrimethylsilane → 2-Trimethylsilylthiazole

Temperature

-78 °C

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.

1. stirringThis mixture was stirred at -78° C. for 1 hour
2. temperaturewarmed to -30° C. over 1 hour
3. wait0° C. over 1/2 hour
4. waitkept at 0° C. for 1 hour
5. customThe reaction was quenched with 50 ml of 50% saturated sodium bicarbonate
6. additiondiluted with 50 ml of ether
7. washThe ether solution was washed with 50 ml of brine
8. customdried
9. filtrationfiltered
10. customevaporated

ORD record

ord-f5f57c2909fe49a196553048155761c7

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05106835