Potassium cyclooctadienide → (Tetramethylcyclopentadienyl)dimethylsilyl(cyclooctadiene)

HRID 399293Notes

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

Participants

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

customA precipitate formed
filtrationafter which time the reaction mixture was filtered
customthe solvents removed under reduced pressure
extractionThe residue was extracted with hexane
filtrationfiltered
customThe solvents were again removed under reduced pressure
customleaving the desired isomeric product

Sources & evidence

ORD record: ord-16b990876e75442d94fcff68c8b17887
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05817849

Reaction notes

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