Sodium Carbonate → HCID 86708422, compound

HRID 1528008Notes

Reaction equation

HRID 1528008 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:36]1[CH:41]=[C:40]([CH3:42])[CH:39]=[C:38]([Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:37]=1)([C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:26]=1)[C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=1.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH3:42][C:40]1[CH:39]=[C:38]([Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:37]=[C:36]([Si:13]([C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=2)([C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([Si:32]([CH3:33])([CH3:34])[CH3:35])[CH:26]=2)[C:8]2[CH:7]([CH3:9])[C:6]([CH3:10])=[C:5]([CH3:11])[C:4]=2[CH3:3])[CH:41]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 82127Potassium hydrideHCID 1381631,2,3,4-TetramethylcyclopentadieneHCID 516892Sodium BicarbonateHCID 86708423HCID 86708423, compound

Product 1

HCID 86708422HCID 86708422, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Under a nitrogen atmosphere, potassium hydride (0.88 g, 21.82 mmol in terms of potassium hydride) dispersed in mineral oil was washed with hexane. Tetrahydrofuran (38 mL) was added and this mixture was warmed to 50° C. A solution of 1,2,3,4-tetramethylcyclopenta-1,3-diene (2.00 g, 16.37 mmol) dissolved in tetrahydrofuran (8 mL) was added dropwise and stirred at 50° C. for one hour. To this solution, a solution of chlorotris(5-methyl-3-trimethylsilyl-phenyl)silane (7.81 g, 14.11 mmol) dissolved in tetrahydrofuran (38 mL) was added dropwise and stirred at 65° C. for 3 hours. The resultant mixture was added dropwise at 0° C. to a solution of a 10% sodium hydrogen carbonate (38 mL) and a 10% sodium carbonate (38 mL). Toluene (38 mL) was added to separate an organic phase, and the organic phase was dried over sodium sulfate and then filtrated. The solvent was removed under reduced pressure. Purification was performed by silica gel column chromatography to obtain 1-tris(5-methyl-3-trimethylsilyl-phenyl)silyl-2,3,4,5-tetramethylcyclopentadiene (5.40 g, yield 59.9%).

Workup

  1. washwas washed with hexane
  2. additionTetrahydrofuran (38 mL) was added
  3. additionwas added dropwise
  4. additionwas added dropwise
  5. stirringstirred at 65° C. for 3 hours
  6. customto separate an organic phase
  7. dry with materialthe organic phase was dried over sodium sulfate
  8. filtrationfiltrated
  9. customThe solvent was removed under reduced pressure
  10. customPurification

Sources & evidence

ORD record
ord-4e86d2611d2d446cba9280cec4c492be
Source dataset
uspto-grants-2015_07
Patent number
US09090527B2

Reaction notes

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