Chlorotrimethylsilane → Silane, 2,4-cyclopentadien-1-ylidenebis(trimethyl-

HRID 622867

Reaction equation

HRID 622867 reaction equation
[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Na+].Cl[Si:8]([CH3:11])([CH3:10])[CH3:9]>O1CCCC1>[CH3:9][Si:8]([C:1]1([Si:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][CH:3]=[CH:2]1)([CH3:11])[CH3:10].[CH3:9][Si:8]([C:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 78681Sodium, 2,4-cyclopentadien-1-yl-

Product 2

HCID 141813Silane, 2,4-cyclopentadien-1-ylidenebis(trimethyl-HCID 120246731,3-Cyclopentadiene, (trimethylsilyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trimethylsilylcyclopentadiene and bis(trimethylsilyl)cyclopentadiene are prepared by the procedures of Kraihanzel et al., J. Amer. Chem. Soc., 90, 4701 (1968) and I. M. Pribytkova et al., J. of Organometallic Chem., 30, C57-C60 (1971). Sodium cyclopentadienide (44 g, 0.50 mole) is added to 150 ml of tetrahydrofuran. Chlorotrimethylsilane (54 g, 0.5 mole) is added dropwise slowly to the reaction and the stirring is continued for 3 hours. The reaction mixture is poured into 150 ml of cold, distilled water and trimethylsilylcyclopentadiene is extracted into diethyl ether. The extract is rotary evaporated to remove the ethereal solvent and the residue is vacuum distilled to give trimethylsilylcyclopentadiene, b.p. 41° C.-43° C. (16 mm).

Workup

  1. additionThe reaction mixture is poured into 150 ml of cold,
  2. distillationdistilled water and trimethylsilylcyclopentadiene
  3. extractionis extracted into diethyl ether
  4. customThe extract is rotary evaporated
  5. customto remove the ethereal solvent
  6. distillationdistilled

Sources & evidence

ORD record
ord-d42af2836cdc4d4a91d217596954d8b4
Source dataset
uspto-grants-1988_09
Patent number
US04772734

Linked notes

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