Trichloromethylsilane → Tetramethylcyclopentadienyl methyl silicon dichloride

HRID 841111Notes

Reaction equation

HRID 841111 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-cf7da4c08a8b49a2ab659941f2df4ca2
Source dataset
uspto-grants-2002_04
Patent number
US06369253B1

Reaction notes

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