Toluene → HCID 19914426, compound

HRID 1090059Notes

Reaction equation

HRID 1090059 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:34]=[CH:33][C:32]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][C:24]=2[CH:23]=1.C([Li])CCC.Cl[Si:41]([CH3:44])([CH3:43])[CH3:42].C1(C)C=CC=CC=1>C1COCC1>[CH3:42][Si:41]([CH3:44])([CH3:43])[N:25]1[C:24]2[CH:23]=[C:22]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:2]3[CH:3]=[CH:4][C:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[N:12]([Si:41]([CH3:44])([CH3:43])[CH3:42])[C:13]=4[CH:1]=3)[CH:34]=[CH:33][C:32]=2[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2

Participants

6

Reactant 4

HCID 1140TolueneHCID 6397ChlorotrimethylsilaneHCID 19914422HCID 19914422, compoundHCID 178418339Butyllithium2×

Product 1

HCID 19914426HCID 19914426, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,6-bis(carbazol-2-yloxy)hexane (30 g) in dry THF (200 ml) was added butyllithium (56 ml; 1.6M in hexane). Once the butyllithium addition was completed, the solution was heated to reflux for 1.5 hours and then allowed to cool. Chlorotrimethylsilane (12 ml) was added dropwise to the cooled mixture and then heated to reflux for 4 hours. Toluene (150 ml) was added to the cool mixture which was then filtered to remove LiC1. The filtrate was collected and the solvent removed under vacuum leaving a crude gray compound. The crude product was further purified by vacuum distillation to give a white compound (E.1) in an 84% yield.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. temperatureheated
  5. temperatureto reflux for 4 hours
  6. filtrationwas then filtered
  7. customto remove LiC1
  8. customThe filtrate was collected
  9. customthe solvent removed under vacuum
  10. customleaving a crude gray compound
  11. distillationThe crude product was further purified by vacuum distillation
  12. customto give a white compound (E.1) in an 84% yield

Sources & evidence

ORD record
ord-f814e5e241b6474094bf870a972fe611
Source dataset
uspto-grants-1992_01
Patent number
US05081091

Reaction notes

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