Réaction #955969

Équation de réaction

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

Rendement 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)

Rendement 91.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreA dry 250-mL three-neck flask was flushed with N2
2. 2
   Autrevia deoxygenated syringe
3. 3
   Autrevia deoxygenated syringe
4. 4
   Températurethe solution was chilled to 0° C.
5. 5
   workup.STIRRINGstirring
6. 6
   workup.WAITwas continued for 5 minutes, at which
7. 7
   Températurewas cooled back to −78° C
8. 8
   workup.STIRRINGstirring
9. 9
   workup.WAITcontinued for 30 minutes at −76° C
10. 10
    AutreThe cooling bath was removed
11. 11
    Températureto warm to ambient temperature
12. 12
    Températurecool 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
    Extractionextracted with MTBE (150 mL) three times
16. 16
    LavageThe combined organic layer was washed with water two times
17. 17
    Séchagedried over anhydrous magnesium sulfate (MgSO4)
18. 18
    FiltrationAfter the product was filtered
19. 19
    Autrethe solvent was removed by rotary evaporation
20. 20
    AutreThe crude product was purified by precipitation into methanol from a chloroform solution

Mode opératoire

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%).

Source