Chlorotrimethylsilane → HCID 68504426, compound

HRID 1712884Notes

Reaction equation

HRID 1712884 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([CH3:8])[CH2:4][C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2.[H-].[K+].[CH3:21][Si:22](Cl)([CH3:24])[CH3:23]>O1CCCC1>[CH3:8][C:5]1[C:4]([Si:22]([CH3:24])([CH3:23])[CH3:21])=[C:3]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:2]([CH3:1])[C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 82127Potassium hydrideHCID 68506250HCID 68506250, compound

Product 1

HCID 68504426HCID 68504426, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.87 g (3.7 mmol) of 2,3,4-trimethyl-1-(8-quinolyl)cyclopentadiene in 20 ml of tetrahydrofuran was added to a suspension of 0.15 g (3.7 mmol) of potassium hydride in 30 ml of tetrahydrofuran and the mixture was subsequently stirred at room temperature for 6 hours. 0.402 g (3.7 mmol) of trimethylsilyl chloride was added while stirring and the mixture was stirred at room temperature for a further 12 hours. The volatile constituents were distilled off and the residue obtained in this way was distilled. At 126-136° C. and 2×10−2 mbar, 3,4,5-trimethyl-1-(8-quinolyl)-2-trimethylsilylcyclopentadiene distilled over in a yield of 0.455 g (1.5 mmol, 40%).

Workup

  1. stirringwhile stirring
  2. stirringthe mixture was stirred at room temperature for a further 12 hours
  3. distillationThe volatile constituents were distilled off
  4. customthe residue obtained in this way
  5. distillationwas distilled
  6. distillationAt 126-136° C. and 2×10−2 mbar, 3,4,5-trimethyl-1-(8-quinolyl)-2-trimethylsilylcyclopentadiene distilled over in a yield of 0.455 g (1.5 mmol, 40%)

Sources & evidence

ORD record
ord-594f01b4f2044509a35f2c6fd213478d
Source dataset
uspto-grants-2010_09
Patent number
US07795167B2

Reaction notes

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