4-Methylthiazole → 4-Methyl-2-(tributylstannyl)-1,3-thiazole

Temperature

-78 °C

4-Methylthiazole (0.5 ml, 5.50 mmol) was dissolved in Et2O (10 ml) and cooled to −78° C. Methyllithium (1.6 M in hexanes, 5.15 ml, 8.24 mmol) was added slowly and the mixture stirred at −78° C. for 1 hour. Tri-n-butyltin chloride (1.640 ml, 6.05 mmol) was then added slowly, the mixture stirred briefly at −78° C. then allowed to warm to RT and stirred overnight. The reaction mixture was quenched with water and extracted with Et2O. The organic phase was washed with brine, dried over sodium sulphate and evaporated under vacuum to afford the title product as a crude pale yellow oil. The material was used without further purification.

1. stirringthe mixture stirred briefly at −78° C.
2. temperatureto warm to RT
3. stirringstirred overnight
4. customThe reaction mixture was quenched with water
5. extractionextracted with Et2O
6. washThe organic phase was washed with brine
7. dry with materialdried over sodium sulphate
8. customevaporated under vacuum

ORD record

ord-6ca136ae5ab048b2807576e5c37b3ae5

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359381B2