Chlorotrimethylsilane → HCID 53669074, compound

HRID 1736953Notes

Reaction equation

HRID 1736953 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C-:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH3:7].[Li+].[CH3:13][Si:14](Cl)([CH3:16])[CH3:15]>C1COCC1>[CH3:1][Si:2]([CH3:10])([CH3:11])[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH2:7][Si:14]([CH3:16])([CH3:15])[CH3:13]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 86749677HCID 86749677, compound

Product 1

HCID 53669074HCID 53669074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution initially at -35° C. of 3.609 g (20.7 mmol) of lithium (1-(trimethylsilyl)-2,4-dimethylpentadienide) in 30 mL of THF was added about 5 g (-46 mmol) of trimethylsilyl chloride. Copious precipitate formed immediately. After stirring overnight, the solvent was removed and the residue was extracted with pentane. After filtering, the solvent was removed under reduced pressure to give the product as a pale yellow liquid. The yield was 4.05 g, 81.3 percent. Major isomer: 1H NMR (C6D6) δ 5.72 (s, 1H), 5.50 (s, 1H), 1.88 (s, 3H), 1.85 (s, 2H), 1.69 (s, 3H), 0.20 (s, 9H), 0.06 (s, 9H). 13C NMR (C6D6) δ 151.8, 135.6, 128.9, 126.4, 27.8, 24.6, 23.5, 0.7, -0.2.

Workup

  1. customCopious precipitate formed immediately
  2. customthe solvent was removed
  3. extractionthe residue was extracted with pentane
  4. filtrationAfter filtering
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bac1a1ab0eaa4857a953a04ddee1022f
Source dataset
uspto-grants-1996_07
Patent number
US05541349

Reaction notes

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