Trimethyltin chloride → 5-Dodecyl-2-trimethylstannylthiophene

Temperature

-78 °C

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.

1. temperatureto warm to room temperature
2. stirringstirred at room temperature for 30 minutes, before it
3. temperaturewas cooled back to −78° C
4. stirringThis mixture was stirred at −78° C. for 2 hours
5. temperatureto warm to room temperature
6. stirringstirred at room temperature overnight
7. customThe reaction was quenched by water (20 mL)
8. additionthe reaction mixture was diluted with hexane (200 mL)
9. washwashed with water
10. dry with materialdried over Na2SO4
11. concentrationconcentrated on a rotary evaporator
12. customwas directly used in the next step without further purification

ORD record

ord-fc08016ac65742edad441d6d978091f4

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598575B2