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Potassium cyclooctadienide → (Tetramethylcyclopentadienyl)dimethylsilyl(cyclooctadiene)

HRID 1636207
Notes
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Reaction equation

HRID 1636207 reaction equation
[C-]1CCCCC=CC=1.[K+].CC1C(C)=C(C)C([Si](Cl)(C)C)(C)C=1.[CH3:23][C:24]1[C:25]([CH3:42])=[C:26]([CH3:41])[C:27]([Si:30]([CH:33]2[CH:40]=[CH:39][CH2:38][CH2:37][CH2:36][CH:35]=[CH:34]2)([CH3:32])[CH3:31])([CH3:29])[CH:28]=1.CC1C(C)=C(C)C([Si](C2CCCC=CC=C2)(C)C)(C)C=1>C1COCC1>[CH3:23][C:24]1[C:25]([CH3:42])=[C:26]([CH3:41])[C:27]([Si:30]([C:33]2[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]=[CH:35][CH:34]=2)([CH3:32])[CH3:31])([CH3:29])[CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 86753202Potassium cyclooctadienideHCID 131720376(Tetramethylcyclopentadienyl)dimethylchlorosilaneHCID 131720867(Tetramethylcyclopentadienyl)(cylcoocta-2,7-dien-1-yl)dimethylsilaneHCID 131720868(Tetramethylcyclopentadienyl)(cylcoocta-2,4-dien-1-yl)dimethylsilane

Product 1

HCID 131720866(Tetramethylcyclopentadienyl)dimethylsilyl(cyclooctadiene)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Potassium cyclooctadienide (3.42 g, 23.4 mmols) dissolved in about 50 mL of THF was added to a solution of (tetramethylcyclopentadienyl)chloro-dimethylsilane (5.02 g, 23.4 mmols) in about 80 mL of THF at about 25° C. A precipitate formed and the reaction mixture was stirred for about 16 hours at about 25° C., after which time the reaction mixture was filtered and the solvents removed under reduced pressure. The residue was extracted with hexane and filtered. The solvents were again removed under reduced pressure leaving the desired isomeric product comprising (tetramethylcyclopentadienyl)(cylcoocta-2,7-dien-1-yl)dimethylsilane and (tetramethylcyclopentadienyl)(cylcoocta-2,4-dien-1-yl)dimethylsilane.

Workup

  1. customA precipitate formed
  2. filtrationafter which time the reaction mixture was filtered
  3. customthe solvents removed under reduced pressure
  4. extractionThe residue was extracted with hexane
  5. filtrationfiltered
  6. customThe solvents were again removed under reduced pressure
  7. customleaving the desired isomeric product

Sources & evidence

ORD record
ord-e85a07e907f34309b90e82b6bf1032dd
Source dataset
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06034021

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes