Tributyltin Chloride → 2-Methoxy-5-(tributylstannyl)-1,3-thiazole

Temperature

-78 °C

To a stirred solution of 2-methoxythiazole (5 g, 43.4 mmol) in tetrahydrofuran (THF) (50 mL) was added n-BuLi (35.3 mL, 56.4 mmol) and the contents stirred at −78° C. After 15 min, tributylchlorostannane (14.13 mL, 52.1 mmol) was added and the mixture stirred with warming to room temperature over a 3 h period. The reaction mixture was quenched with water (20 mL) and the contents extracted with ether (25 mL). The organic layer was separated and dried over anhydrous sodium sulphate, filtered, and the filtrate concentrated in vacuo to afford the crude product (6 g). The crude product was purified by silica gel column chromatography (eluent: 2% EtOAc/Hexane) to afford 2-methoxy-5-(tributylstannyl)thiazole (4 g, 22%) as yellow liquid. 1H NMR (400 MHz, CDCl3-d3) δ ppm 0.90-0.98 (m, 9H), 1.05-1.15 (m, 6H), 1.30-1.40 (m, 6H), 1.50-1.65 (m, 6H), 4.04 (s, 3H), 7.03 (s, 1H). LCMS (ES) [M+H]+ 405.99.

1. stirringthe mixture stirred
2. temperaturewith warming to room temperature over a 3 h period
3. customThe reaction mixture was quenched with water (20 mL)
4. extractionthe contents extracted with ether (25 mL)
5. customThe organic layer was separated
6. dry with materialdried over anhydrous sodium sulphate
7. filtrationfiltered
8. concentrationthe filtrate concentrated in vacuo
9. customto afford the crude product (6 g)
10. customThe crude product was purified by silica gel column chromatography (eluent: 2% EtOAc/Hexane)

ORD record

ord-465306616b654bd4bb2861205f20ef84

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765792B2