Ammonium Chloride → Dimethyl(2-i-propylindenyl)(2-methyl-4-phenylindenyl)silane

HRID 1953952Notes

Reaction equation

HRID 1953952 reaction equation
[CH:1]([C:4]1[CH2:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([CH3:3])[CH3:2].C([Li])CCC.[CH3:18][Si:19](Cl)([CH3:36])[CH:20]1[C:28]2[C:23](=[C:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[CH3:35].[Cl-].[NH4+]>[Cu]C#N.CCCCCC.C(OCC)C>[CH3:18][Si:19]([CH3:36])([CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[C:4]1[CH:1]([CH3:3])[CH3:2])[CH:20]1[C:28]2[C:23](=[C:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[CH3:35]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 158656612-Isopropyl-1H-indeneHCID 21943894Dimethyl(2-methyl-4-phenylindenyl)silyl chlorideHCID 178418339Butyllithium

Product 1

HCID 23295638Dimethyl(2-i-propylindenyl)(2-methyl-4-phenylindenyl)silaneYield 84.3%

Reagents, catalysts & solvents 3

HCID 178418546HCID 178418546, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

In a 200-ml two-necked flask were charged 4.5 g (28.5 mmol) of 2-i-propylindene, 70.2 mg (0.78 mmol) of copper (I) cyanide, and 150 ml of diethyl ether. To the mixture was added at -78° C. 19.6 ml of 1.6 M hexane solution of n-butyllithium and the mixture was stirred at room temperature for 2 hours. Subsequently, 6.57 g (23.6 mmol) of dimethyl(2-methyl-4-phenylindenyl)silyl chloride was added at -78° C. and the mixture was stirred at room temperature for 12 hours. After addition of aqueous ammonium chloride solution to the reaction mixture, the organic layer was washed with saturated saline and dried over sodium sulfate. The sodium sulfate was removed by filtration and the organic solvent was distilled off under reduced pressure. The residue was purified by column chromatography (silica gel, development solvent: n-hexane: methylene chloride=9:1) to obtain 8.3 g (19.9 mmol, yield: 70%) of a pale yellow oil. The product was confirmed to be a mixture of two isomers by 1H-NMR.

Workup

  1. additionTo the mixture was added at -78° C
  2. washthe organic layer was washed with saturated saline
  3. dry with materialdried over sodium sulfate
  4. customThe sodium sulfate was removed by filtration
  5. distillationthe organic solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, development solvent: n-hexane: methylene chloride=9:1)

Sources & evidence

ORD record
ord-50c48c829ea24241a77e2bfe07450120
Source dataset
uspto-grants-2000_09
Patent number
US06121182

Reaction notes

Loading…