Oxygen → 3,6-Bis(triisopropylsilyl)-9H-carbazole

HRID 2045149Notes

Reaction equation

HRID 2045149 reaction equation
C([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])[CH:13]=2)C1C=CC=CC=1.C1COCC1.O=O>CS(C)=O>[CH:38]([Si:31]([CH:32]([CH3:34])[CH3:33])([CH:35]([CH3:37])[CH3:36])[C:12]1[CH:11]=[CH:10][C:9]2[NH:8][C:20]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][C:17]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:28]([CH3:30])[CH3:29])[CH:22]([CH3:23])[CH3:24])=[CH:18][CH:19]=3)([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 977OxygenHCID 8028TetrahydrofuranHCID 583898579-Benzyl-3,6-bis(triisopropylsilyl)-9H-carbazole

Product 1

HCID 583898523,6-Bis(triisopropylsilyl)-9H-carbazoleYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

A 500 ml dry round bottom flask was charged with 9-benzyl-3,6-bis-triisopropylsilanyl-9H-carbazole 4 (23.0 g, 0.04 mol) and the oil was suspended in 100 ml DMSO. The suspension was cooled in an ice water bath (˜15° C.) and 1M KOBu-t in THF (240 ml, 0.24 mol) was added via a syringe under nitrogen. Oxygen started to bubble in the mixture and the nitrogen line was suppressed. While the oxygen bubbling was taking place, the mixture was left to warm up to ˜20° C. and cooling continued with only water. The oxygen bubbling continued until the starting material (TLC) disappeared, i.e., after ˜30 min. Water was added to the mixture and the mixture was extracted with 5×200 ml ethylacetate. To remove the benzoic acid organic layer, the mixture was washed with sat. NaHCO3, followed by brine washing. The organic layer was then dried over Na2SO4, filtered, concentrated, and purified over a 330 g SiO2 column with hexane and hexane:ethylacetate (95:5) eluents. Appropriate fractions were collected to yield a white solid of 3,6-bis-triisopropylsilanyl-carbazole 5 10.0 g (54%).

Workup

  1. customA 500 ml dry round bottom flask
  2. additionwas added via a syringe under nitrogen
  3. customto bubble in the mixture
  4. waitthe mixture was left
  5. temperaturecooling
  6. additionWater was added to the mixture
  7. extractionthe mixture was extracted with 5×200 ml ethylacetate
  8. customTo remove the benzoic acid organic layer
  9. washthe mixture was washed with sat. NaHCO3
  10. dry with materialThe organic layer was then dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. custompurified over a 330 g SiO2 column with hexane and hexane:ethylacetate (95:5) eluents
  14. customAppropriate fractions were collected

Sources & evidence

ORD record
ord-18a5f07b3e4e459ab271d2d9ddee3519
Source dataset
uspto-grants-2013_11
Patent number
US08586973B2

Reaction notes

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