Reacción #955969

Ecuación de reacción

4-(3-ethylhept-1-yn-1-yl)-8-(3-ethylnon-1-yn-1-yl)benzo[1,2-b:4,5-b′]dithiophene

Triisopropylsilyl chloride

tert-butyllithium

→

solid

Rendimiento 91.0%

(4-(3-ethylhept-1-yn-1-yl)-8-(3-ethylnon-1-yn-1-yl)benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl)bis(triisopropylsilane)

Rendimiento 91.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA dry 250-mL three-neck flask was flushed with N2
2. 2
   Otrovia deoxygenated syringe
3. 3
   Otrovia deoxygenated syringe
4. 4
   Temperaturathe solution was chilled to 0° C.
5. 5
   workup.STIRRINGstirring
6. 6
   workup.WAITwas continued for 5 minutes, at which
7. 7
   Temperaturawas cooled back to −78° C
8. 8
   workup.STIRRINGstirring
9. 9
   workup.WAITcontinued for 30 minutes at −76° C
10. 10
    OtroThe cooling bath was removed
11. 11
    Temperaturato warm to ambient temperature
12. 12
    Temperaturacool DI water (20 mL)
13. 13
    workup.ADDITIONwas slowly added to the reaction flask
14. 14
    workup.ADDITIONThen, the reaction mixture was poured into 100 mL of cool water
15. 15
    Extracciónextracted with MTBE (150 mL) three times
16. 16
    LavadoThe combined organic layer was washed with water two times
17. 17
    Secadodried over anhydrous magnesium sulfate (MgSO4)
18. 18
    FiltraciónAfter the product was filtered
19. 19
    Otrothe solvent was removed by rotary evaporation
20. 20
    OtroThe crude product was purified by precipitation into methanol from a chloroform solution

Procedimiento

A dry 250-mL three-neck flask was flushed with N2 and was charged with 4-(3-ethylhept-1-yn-1-yl)-8-(3-ethylnon-1-yn-1-yl)benzo[1,2-b:4,5-b′]dithiophene (2.0 g, 4.6 mmol) and THF (100 mL, 0.05 M) via deoxygenated syringe. The reaction flask was cooled to −78° C. and a 1.3 M solution of tert-butyllithium in hexanes (8.8 mL, 0.012 mol) was added drop-wise via deoxygenated syringe. After 30 minutes of stirring at −78° C., the solution was chilled to 0° C. and stirring was continued for 5 minutes, at which point the reaction mixture was cooled back to −78° C. Triisopropylsilyl chloride (4.0 mL, 0.018 mol) was added to the reaction flask drop-wise and stirring continued for 30 minutes at −76° C. The cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature. As the reaction was completed, cool DI water (20 mL) was slowly added to the reaction flask. Then, the reaction mixture was poured into 100 mL of cool water and extracted with MTBE (150 mL) three times. The combined organic layer was washed with water two times and dried over anhydrous magnesium sulfate (MgSO4). After the product was filtered, the solvent was removed by rotary evaporation. The crude product was purified by precipitation into methanol from a chloroform solution to yield white solid (3.13 g, 91%).

Fuente