Sodium Carbonate → HCID 123427119, compound

HRID 1528009Notes

Reaction equation

HRID 1528009 reaction equation
[H-].[K+].[CH3:3][C:4]1[CH2:8][C:7]([CH3:9])=[C:6]([CH3:10])[C:5]=1[CH3:11].Cl[Si:13]([C:42]1[CH:47]=[C:46]([Si:48]([CH3:51])([CH3:50])[CH3:49])[CH:45]=[C:44]([Si:52]([CH3:55])([CH3:54])[CH3:53])[CH:43]=1)([C:28]1[CH:33]=[C:32]([Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:31]=[C:30]([Si:38]([CH3:41])([CH3:40])[CH3:39])[CH:29]=1)[C:14]1[CH:19]=[C:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:17]=[C:16]([Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:15]=1.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH3:39][Si:38]([CH3:41])([CH3:40])[C:30]1[CH:29]=[C:28]([Si:13]([C:42]2[CH:43]=[C:44]([Si:52]([CH3:55])([CH3:54])[CH3:53])[CH:45]=[C:46]([Si:48]([CH3:51])([CH3:50])[CH3:49])[CH:47]=2)([C:14]2[CH:19]=[C:18]([Si:20]([CH3:21])([CH3:22])[CH3:23])[CH:17]=[C:16]([Si:24]([CH3:26])([CH3:25])[CH3:27])[CH:15]=2)[C:8]2[CH:7]([CH3:9])[C:6]([CH3:10])=[C:5]([CH3:11])[C:4]=2[CH3:3])[CH:33]=[C:32]([Si:34]([CH3:35])([CH3:36])[CH3:37])[CH:31]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 82127Potassium hydride2×HCID 1381631,2,3,4-TetramethylcyclopentadieneHCID 516892Sodium BicarbonateHCID 88962872HCID 88962872, compound

Product 1

HCID 123427119HCID 123427119, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
50 °C

Procedure

Under a nitrogen atmosphere, to potassium hydride dispersed in mineral oil (1.19 g, 29.78 mmol in terms of potassium hydride), tetrahydrofuran (108 mL) was added. This mixture was warmed to 50° C. and a solution of 1,2,3,4-tetramethylcyclopenta-1,3-diene (2.73 g, 22.34 mmol) dissolved in tetrahydrofuran (27 mL) was added dropwise. Stirring was performed at 50° C. for 1 hour. To this solution, a solution of chlorotris{3,5-bis(trimethysilyl)phenyl}silane (13.55 g, 18.62 mmol) dissolved in tetrahydrofuran (27 mL) was added dropwise and stirred at 50° C. for 5 hours. The resultant mixture was added dropwise at 0° C. to a solution of 10% sodium hydrogen carbonate (68 ml) and 10% sodium carbonate (68 mL). Toluene (68 mL) was added to separate an organic phase. After dried over sodium sulfate, the organic phase was filtrated. The solvent was removed under reduced pressure. Hexane was added and the obtained white solid was filtrated to obtain 1-tris{3,5-bis(trimethylsilyl)phenyl}silyl-2,3,4,5-tetramethylcyclopentadiene (7.01 g, yield 46.2%).

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. additionwas added dropwise
  4. stirringstirred at 50° C. for 5 hours
  5. customto separate an organic phase
  6. dry with materialAfter dried over sodium sulfate
  7. filtrationthe organic phase was filtrated
  8. customThe solvent was removed under reduced pressure
  9. additionHexane was added
  10. filtrationthe obtained white solid was filtrated

Sources & evidence

ORD record
ord-2b10d910b907469fb70d1dbbc894a658
Source dataset
uspto-grants-2015_07
Patent number
US09090527B2

Reaction notes

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