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

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence