Chlorotrimethylsilane → 1,3-Bis(trimethylsilyl)cyclopentadiene

HRID 622868Notes

Reaction equation

HRID 622868 reaction equation
[CH3:1][Si:2]([C:5]1[CH2:9][CH:8]=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C([Li])CCC.Cl[Si:16]([CH3:19])([CH3:18])[CH3:17]>>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]1[CH2:9][CH:8]=[C:7]([Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1

Participants

4

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 120246731,3-Cyclopentadiene, (trimethylsilyl)-HCID 178418339Butyllithium

Product 1

HCID 121615891,3-Bis(trimethylsilyl)cyclopentadiene

Conditions

Temperature
40 °C

Procedure

Freshly distilled trimethylsilylcyclopentadiene (1.6 g, 11.5 mmole) is dissolved in 10 ml of absolute ligroin. To this solution is added a solution of butyllithium (1.9N, 6.35 ml, 12.0 mmole) in ligroin dropwise with stirring. The mixture is stirred for one hour at room temperature. Chlorotrimethylsilane (2.6 g, 24 mmole) is added to the mixture under an argon sweep, and the resulting mixture heated for 3 hours at 40° C. The ligroin solution is filtered, the solvent evaporated, and the residue distilled under a vacuum to give 1,3-bis(trimethylsilyl)cyclopentadiene, b.p. 45° C./3 mm Hg.

Workup

  1. stirringThe mixture is stirred for one hour at room temperature
  2. filtrationThe ligroin solution is filtered
  3. customthe solvent evaporated
  4. distillationthe residue distilled under a vacuum

Sources & evidence

ORD record
ord-aa30ed8be72d4070bc210ec011305abc
Source dataset
uspto-grants-1988_09
Patent number
US04772734

Reaction notes

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