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

HRID 1446363Notes

Reaction equation

HRID 1446363 reaction equation
[CH3:1][C:2]1[CH2:6][C:5]([CH3:7])=[C:4]([CH3:8])[C:3]=1[CH3:9].[Li]CCCC.[Cl:15][Si:16](Cl)([CH3:18])[CH3:17]>C1COCC1>[Cl:15][Si:16]([CH3:18])([CH3:17])[CH:6]1[C:5]([CH3:7])=[C:4]([CH3:8])[C:3]([CH3:9])=[C:2]1[CH3:1]

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

Under an argon atmosphere, to a solution of 48.0 g (0.393 mol) of tetramethylcyclopentadiene in 600 ml of THF, 157 ml of 2.5 M (0.393 mol) nBuLi in hexanes were added dropwise over 20 minutes at −80° C. This mixture was additionally stirred for 20 minutes at this temperature, and then for 0.5 hours at room temperature. The resulting mixture was added dropwise over 1.5 hours to a solution of 86.3 g (0.669 mol) of dichlorodimethylsilane in 150 ml of THF. The resulting mixture was stirred overnight at ambient temperature and then evaporated to dryness. Fractional distillation gave a yellow liquid, bp 52-56° C./1 mm Hg. Yield 48.3 g (57%).

Workup

  1. waitfor 0.5 hours at room temperature
  2. stirringThe resulting mixture was stirred overnight at ambient temperature
  3. customevaporated to dryness
  4. distillationFractional distillation
  5. customgave a yellow liquid, bp 52-56° C./1 mm Hg

Sources & evidence

ORD record
ord-8c7bbf6559fd426fa95257d5e39e7bd0
Source dataset
uspto-grants-2010_02
Patent number
US07667064B2

Reaction notes

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