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

Temperature

0 °C

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.

1. stirringstirred for 1 h
2. temperatureThe reaction mixture was then cooled to −78° C.
3. stirringThe reaction mixture was stirred for 30 minutes
4. temperatureto warm to room temperature
5. stirringstirred for 16 h
6. customThe reaction was quenched with water (20 mL)
7. extractionextracted with ethyl acetate (2×50 mL)
8. dry with materialThe combined organic layer was dried over sodium sulfate
9. filtrationfiltered
10. customevaporated in vacuo

ORD record

ord-42d508d8d0d447b892468ef1a1831018

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2