Chlorotrimethylsilane → HCID 53648471, compound

HRID 1736952Notes

Reaction equation

HRID 1736952 reaction equation
[CH3:1][C:2]([CH:4]=[C:5]([CH3:7])[CH3:6])=[CH-:3].[K+].[CH3:9][Si:10](Cl)([CH3:12])[CH3:11]>C1COCC1>[CH3:9][Si:10]([CH3:12])([CH3:11])[CH2:3][C:2]([CH3:1])=[CH:4][C:5]([CH3:7])=[CH2:6]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 22924518HCID 22924518, compound

Product 1

HCID 53648471HCID 53648471, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 15.1 g (112 mmol) of potassium 2,4-dimethylpentadienide in 250 mL of THF was added to a -35° C. solution of 36.0 g (33.1 mmol) of trimethylsilyl chloride in 200 mL of THF. The yellow-orange color of the pentadienyl anion faded instantly upon addition. The reaction mixture was stirred overnight. The solvent was removed under reduced pressure, the residue was extracted with pentane, the resulting solution was filtered from insolubles and concentrated under reduced pressure to give the product as a pale yellow liquid. The yield was 11.65g, 61.5%. 1H NMR(C6D6) δ 5.63 (s, 1H), 4.95 (s, 1H), 4.92 (s, 1H), 1.83 (s, 3H), 1.81 (s, 2H), 1.68 (s, 3H), 0.03 (s, 9H). 13C NMR (C6D6) δ 142.5, 136.0 125.2, 113.1, 27.8, 24.5, -0.2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe residue was extracted with pentane
  3. filtrationthe resulting solution was filtered from insolubles
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45fa35a0eab244e1928defa21e73a45f
Source dataset
uspto-grants-1996_07
Patent number
US05541349

Reaction notes

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