Dichlorodimethylsilane → HCID 23295621, compound

HRID 1953960Notes

Reaction equation

HRID 1953960 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6]([C:9]1[CH2:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:8])[CH3:7].[CH3:24][Si:25]([CH3:28])(Cl)Cl.[Cl-].[NH4+]>[Cu]C#N.CCCCCC.C(OCC)C>[CH3:24][Si:25]([CH3:28])([CH:17]1[C:16]2[C:11](=[C:12]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:6]([CH3:8])[CH3:7])[CH:1]1[C:22]2[C:4](=[C:18]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:11]=3)[CH:19]=[CH:20][CH:21]=2)[CH:3]=[C:2]1[CH:6]([CH3:8])[CH3:7]

Participants

8

Reactant 4

HCID 6398DichlorodimethylsilaneHCID 25517Ammonium ChlorideHCID 23295619HCID 23295619, compoundHCID 178418339Butyllithium

Product 1

HCID 23295621HCID 23295621, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 178418546HCID 178418546, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent2×

Procedure

Under nitrogen atmosphere, 24.5 ml of 1.63 M hexane solution of n-butyllithium (40 mmol) was dripped down at -78° C. into 90 ml of a diethyl ether suspension of 9.37 g (40.0 mmol) of 2-i-propyl-7-phenylindene and 0.1 g (1.0 mmol) of copper (I) cyanide. After completion of the dripping, the temperature was slowly elevated to room temperature and the mixture was stirred at room temperature for 2 hours. Again, the mixture was cooled down to -78° C. and 2.58 g (20.0 mmol) of dimethyldichlorosilane was added thereto slowly. After completion of the dripping, the temperature was slowly elevated to room temperature, and the mixture was stirred for 7 hours. The reaction mixture was poured into aqueous saturated ammonium chloride solution and extracted with diethyl ether. After it was washed with saturated saline, the organic phase was dried over anhydrous magnesium sulfate, followed by distilling off the solvent to obtain viscous solids. The solids were fractionated by column chromatography (silica gel, development solvent: n-hexane) to obtain 9.69 g (18.5 mmol, yield: 92.5%) of dimethylbis(2-i-propyl-4-phenylindenyl)silane. By 1H-NMR, this was confirmed to be a mixture of two isomers.

Workup

  1. customwas slowly elevated to room temperature
  2. temperatureAgain, the mixture was cooled down to -78° C.
  3. customwas slowly elevated to room temperature
  4. stirringthe mixture was stirred for 7 hours
  5. extractionextracted with diethyl ether
  6. washAfter it was washed with saturated saline
  7. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  8. distillationby distilling off the solvent
  9. customto obtain viscous solids

Sources & evidence

ORD record
ord-560593e5b2e54c679999e975cd05955b
Source dataset
uspto-grants-2000_09
Patent number
US06121182

Reaction notes

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