Dichlorodimethylsilane → Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silane

HRID 441104Notes

Reaction equation

HRID 441104 reaction equation
[CH3:1][C:2]1[CH2:6][C:5]([CH3:7])=[C:4]([CH3:8])[C:3]=1[CH3:9].C([Li])CCC.[CH3:15][Si:16]([CH3:19])(Cl)[Cl:17]>C1COCC1>[CH3:7][C:5]1[CH:6]([Si:16]([CH3:19])([CH3:15])[Cl:17])[C:2]([CH3:1])=[C:3]([CH3:9])[C:4]=1[CH3:8]

Participants

5

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 1381631,2,3,4-TetramethylcyclopentadieneHCID 178418339Butyllithium

Product 1

HCID 5045335Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.0 g (32.8 mmol) of 1,2,3,4-tetramethylcyclopentadiene (F. X. Kohl; P. Jutzi, J. Organomet. Chem. 243 (1983) 119-121; G. Schmitt, S. Ozman, Chemikerzeitung 100 (1976), 143; E. E. Bunel; P. Campos, J. Ruz; L. Valle, Organometallics 7 (1988), 1828-1838; C. M. Fendrick; L. D. Schertz; V. W. Day; T. J. Marks, Organometallics 7, (1988) 1828-1838 and literature cited therein) are dissolved in 50 ml of absolute THF and admixed with 21 ml of n-butyllithium (1.6M in pentane, 33.6 mmol). The mixture is stirred for 2 hours and 4.50 g (33.3 mmol) of dimethyldichlorosilane, dissolved in 30 ml of absolute THF, are then added dropwise at 0° C. The mixture is subsequently stirred for a further 20 hours. After removal of the solvent in vacuo and filtering off the lithium chloride formed during the reaction, the residue is vacuum distilled. Bp: 57°-65° C. (P=0.1 torr).

Workup

  1. additionare then added dropwise at 0° C
  2. stirringThe mixture is subsequently stirred for a further 20 hours
  3. customAfter removal of the solvent in vacuo
  4. filtrationfiltering off the lithium chloride
  5. customformed during the reaction
  6. distillationdistilled

Sources & evidence

ORD record
ord-3c41bf2a3b2b46acbfa13f50f7c84a6a
Source dataset
uspto-grants-1996_05
Patent number
US05521265

Reaction notes

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