Tetrahydrofuran → 3,3'-Di-n-hexylsilylene-2,2'-bithiophene

Temperature

-78 °C

To a solution of n-BuLi in hexane (60 mmol, 24 mL) in anhydrous THF (500 mL) at −78° C. was added dropwise under vigorous stirring a solution of 11 (30 mmol, 9.720 g) in anhydrous THF (100 mL) over 30 min. The mixture was then stirred at −78° C. for 1 h, resulting in a white suspension. Next, a solution of dichlorodihexylsilane (30 mmol, 8.070 g) in THF (100 mL) was added dropwise. The reaction mixture was stirred at −78° C. for five additional hours, allowed to warm to room temperature, and stirred overnight. The reaction was next quenched by adding saturated aqueous NH4Cl solution (300 mL). The aqueous layer was extracted with ether (3×100 mL). The organic phases were then combined and washed with water and dried over MgSO4. After filtration, the solvent was removed, and the crude product was purified by column chromatography to yield a light yellow liquid (6.8 g, 68%). 1H NMR (CDCl3): δ 0.85-0.93 (m, 10H), 1.24-1.41 (m, 16H), 7.06 (d, 2H, J=5 Hz), 7.21 (d, 2H, J=5 Hz) ppm; 13C NMR (CDCl3): δ 12.07, 14.29, 22.80, 24.37, 31.65, 33.07, 125.17, 126.85, 141.81, 149.37 ppm.

1. customresulting in a white suspension
2. stirringThe reaction mixture was stirred at −78° C. for five additional hours
3. temperatureto warm to room temperature
4. stirringstirred overnight
5. customThe reaction was next quenched
6. additionby adding saturated aqueous NH4Cl solution (300 mL)
7. extractionThe aqueous layer was extracted with ether (3×100 mL)
8. washwashed with water
9. dry with materialdried over MgSO4
10. filtrationAfter filtration
11. customthe solvent was removed
12. customthe crude product was purified by column chromatography

ORD record

ord-d5d23a7a255447eea2f712a7f674278a

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07605225B2