Chlorotrimethylsilane → 1,3-Bis(trimethylsilyl)cyclopentadiene

HRID 2413506Notes

Reaction equation

HRID 2413506 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-36b4baf6342144edba7855c399ff7018
Source dataset
uspto-grants-1988_01
Patent number
US04717783

Reaction notes

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