Trimethyltin chloride → 5-Dodecyl-2-trimethylstannylthiophene

Participants

Reaction Conditions

Reaction Steps

A solution of 2-dodecylthiophene (5.18 g, 20.5 mmol) in dry THF (90 mL) was cooled to −78° C., and a solution of n-BuLi (2.5 M, 12.3 mL, 30.8 mmol) was then added slowly. This mixture was stirred at −78° C. for additiona 10 minutes, and then allowed to warm to room temperature and stirred at room temperature for 30 minutes, before it was cooled back to −78° C. A solution of trimethylstannyl chloride (1.0 M, 31 mL, 31.0 mmol) was added slowly. This mixture was stirred at −78° C. for 2 hours, and then allowed to warm to room temperature, and stirred at room temperature overnight. The reaction was quenched by water (20 mL), and the reaction mixture was diluted with hexane (200 mL), washed with water, dried over Na2SO4, and concentrated on a rotary evaporator, leading to a slightly yellow oil (8.35 g, 98.0%), which was directly used in the next step without further purification.

Provenance & Evidence