Trichloromethylsilane → Tetramethylcyclopentadienyl methyl silicon dichloride

HRID 1004419Notes

Reaction equation

HRID 1004419 reaction equation
[CH3:1][C:2]1[CH:3]([Li])[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[CH3:11][Si:12](Cl)([Cl:14])[Cl:13]>C1COCC1>[CH3:1][C:2]1[CH:3]([Si:12]([Cl:14])([Cl:13])[CH3:11])[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 6399TrichloromethylsilaneHCID 178506838Lithium tetramethylcyclopentadienide

Product 1

HCID 11322281Tetramethylcyclopentadienyl methyl silicon dichlorideYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(2,3,4,5-Tetramethylcyclopentadienyl)lithium (1.33 g, 10.37 mmol) was dissolved in 80 mL THF and cooled to -78° C., and MeSiCl3 (1.70 g, 11.4 mmol) was added via a syringe. After addition, the cooling bath was removed and the reaction mixture was stirred at room temperature for 16 h. Volatiles were removed under vacuum at room temperature, and the residue was extracted twice with hexanes (2×20 mL). The hexane fractions were combined and the solvent was removed under vacuum to give a pale yellow oil (tetramethylcyclopentadienyl methyl silicon dichloride); 2.0 g, 82% yield. 1H-NMR (C6D6): δ(ppm): 2.95 (broad s, 1 H; Me4CpH), 1.92 (s, 6H;), 1.63 (s, 6H; Me4Cp), 0.19 (s, 3 H; MeSi).

Workup

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. customVolatiles were removed under vacuum at room temperature
  4. extractionthe residue was extracted twice with hexanes (2×20 mL)
  5. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-52b7d38e118b4834a08c38f752502ffc
Source dataset
uspto-grants-2000_04
Patent number
US06048992

Reaction notes

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