Triisopropylsilyl chloride → HCID 67054652, compound

HRID 868787Notes

Reaction equation

HRID 868787 reaction equation
[CH2:1]([CH:3]([CH2:29][CH2:30][CH2:31][CH3:32])[C:4]#[C:5][C:6]1[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[C:12]([C:18]#[C:19][CH:20]([CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:8]2[S:9][CH:10]=[CH:11][C:7]=12)[CH3:2].[C:33]([Li])([CH3:36])([CH3:35])C.[CH:38]([Si:41](Cl)([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])([CH3:40])[CH3:39]>C1COCC1>[CH2:1]([CH:3]([CH2:29][CH2:30][CH2:31][CH3:32])[C:4]#[C:5][C:6]1[C:14]2[S:15][C:16]([Si:41]([CH:42]([CH3:44])[CH3:43])([CH:33]([CH3:36])[CH3:35])[CH:38]([CH3:40])[CH3:39])=[CH:17][C:13]=2[C:12]([C:18]#[C:19][CH:20]([CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:8]2[S:9][C:10]([Si:41]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:38]([CH3:40])[CH3:39])=[CH:11][C:7]=12)[CH3:2]

Participants

5

Reactant 3

HCID 139400Triisopropylsilyl chlorideHCID 58401206HCID 58401206, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 67054652HCID 67054652, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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%).

Workup

  1. customA dry 250-mL three-neck flask was flushed with N2
  2. customvia deoxygenated syringe
  3. customvia deoxygenated syringe
  4. temperaturethe solution was chilled to 0° C.
  5. stirringstirring
  6. waitwas continued for 5 minutes, at which
  7. temperaturewas cooled back to −78° C
  8. stirringstirring
  9. waitcontinued for 30 minutes at −76° C
  10. customThe cooling bath was removed
  11. temperatureto warm to ambient temperature
  12. temperaturecool DI water (20 mL)
  13. additionwas slowly added to the reaction flask
  14. additionThen, the reaction mixture was poured into 100 mL of cool water
  15. extractionextracted with MTBE (150 mL) three times
  16. washThe combined organic layer was washed with water two times
  17. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  18. filtrationAfter the product was filtered
  19. customthe solvent was removed by rotary evaporation
  20. customThe crude product was purified by precipitation into methanol from a chloroform solution

Sources & evidence

ORD record
ord-05427d851ac7485c95bc5b8bf115b440
Source dataset
uspto-grants-2015_03
Patent number
US08968885B2

Reaction notes

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