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

HRID 1953961
Notes
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Reaction equation

HRID 1953961 reaction equation
[CH:1]([C:4]1[CH2:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:9]=[CH:8][CH:7]=2)([CH3:3])[CH3:2].C([Li])CCC.[CH3:24][Si:25](Cl)([CH3:42])[CH:26]1[C:34]2[C:29](=[C:30]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1[CH3:41].[Cl-].[NH4+]>[Cu](C#N)C#N.CCCCCC.C(OCC)C>[CH3:24][Si:25]([CH3:42])([CH:5]1[C:6]2[C:11](=[C:10]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:9]=[CH:8][CH:7]=2)[CH:12]=[C:4]1[CH:1]([CH3:3])[CH3:2])[CH:26]1[C:34]2[C:29](=[C:30]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1[CH3:41]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 180082381H-Indene, 2-(1-methylethyl)-4-phenyl-HCID 21943894Dimethyl(2-methyl-4-phenylindenyl)silyl chlorideHCID 178418339Butyllithium

Product 1

HCID 23295617Dimethyl(2-i-propyl-4-phenylindenyl)(2-methyl-4-phenylindenyl)silaneYield 77.7%

Reagents, catalysts & solvents 3

HCID 178418260HCID 178418260, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

In a 200-ml two-necked flask were charged 7.38 g (31.5 mmol) of 2-i-propyl-4-phenylindene, 55.3 mg (0.618 mmol) of copper cyanide and 100 ml of dry diethyl ether. To the mixture was added at -78° C., 22.0 ml of 1.62 M hexane solution of n-butyllithium (35.2 mmol) and the mixture was stirred at room temperature for 2 hours. Subsequently, 8.46 g (28.3 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 it was poured into aqueous ammonium chloride, the reaction mixture was extracted with diethyl ether. 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, eluent: n-hexane, methylene chloride) to obtain 10.93 g (22.0 mmol, yield: 77.7%) of a pale yellow liquid. 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. extractionthe reaction mixture was extracted with diethyl ether
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over sodium sulfate
  5. customThe sodium sulfate was removed by filtration
  6. distillationthe organic solvent was distilled off under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel, eluent: n-hexane, methylene chloride)

Sources & evidence

ORD record
ord-29c9a9d8596f444bbc2e531fe185c075
Source dataset
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06121182

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes