Trimethyltin chloride → (S)-2-(2-methylbutyl)-5-trimethylstannylfuran

Temperature

-78 °C

A solution of (S)-2-(2-methylbutyl)furan (4.10 g, 29.7 mmol) in dry THF (100 mL) was cooled to −78° C., and a solution of n-BuLi (2.5 M, 18.0 mL, 45.0 mmol) was then added slowly. This mixture was stirred at −78° C. for additional 20 minutes, and then allowed to warm to room temperature and stirred at room temperature for 60 minutes, before it was cooled back to −78° C. A solution of trimethylstannyl chloride (1.0 M, 45 mL, 45.0 mmol) was added slowly. This mixture was stirred at −78° C. for 1 hour, and then allowed to warm to room temperature, and stirred at room temperature overnight. The reaction was quenched by water (20 mL), and reaction mixture was diluted with hexane (300 mL), washed with water (200 mL×2), dried over Na2SO4, and concentrated on a rotary evaporator, leading to a slightly yellow oil (7.43 g, 83.2%).

1. temperatureto warm to room temperature
2. stirringstirred at room temperature for 60 minutes, before it
3. temperaturewas cooled back to −78° C
4. stirringThis mixture was stirred at −78° C. for 1 hour
5. temperatureto warm to room temperature
6. stirringstirred at room temperature overnight
7. customThe reaction was quenched by water (20 mL), and reaction mixture
8. additionwas diluted with hexane (300 mL)
9. washwashed with water (200 mL×2)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated on a rotary evaporator

ORD record

ord-91377d4b5fb9437fa8a035020a5f0857

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598575B2