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Ammonium Chloride → Dimethyl-(6-methyl-4,8-diphenyl-1,2,3,5-tetrahydro-s-indacenyl)(2-i-propyl-4-(4-t-butylphenyl)-1-indenyl)silane

HRID 271801
Notes
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Reaction equation

HRID 271801 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:5]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:6]3[C:10](=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:12]=2[CH:13]=1)[CH2:9][CH2:8][CH2:7]3.C([Li])CCC.Cl[Si:32]([CH:35]1[C:43]2[C:38](=[C:39]([C:44]3[CH:49]=[CH:48][C:47]([C:50]([CH3:53])([CH3:52])[CH3:51])=[CH:46][CH:45]=3)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[C:36]1[CH:54]([CH3:56])[CH3:55])([CH3:34])[CH3:33].[Cl-].[NH4+]>C(OCC)C.C1COCC1.CCCCCC.[Cu](C#N)C#N>[CH3:33][Si:32]([CH3:34])([CH:7]1[C:6]2[C:10](=[C:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:12]3[CH2:13][C:2]([CH3:1])=[CH:3][C:4]=3[C:5]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:9][CH2:8]1)[CH:35]1[C:43]2[C:38](=[C:39]([C:44]3[CH:45]=[CH:46][C:47]([C:50]([CH3:51])([CH3:52])[CH3:53])=[CH:48][CH:49]=3)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[C:36]1[CH:54]([CH3:55])[CH3:56]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 25517Ammonium ChlorideHCID 21880365chloro-(4-(4-tert-butylphenyl)-2-isopropyl-1H-inden-1-yl)-dimethylsilaneHCID 860577626-Methyl-4,8-diphenyl-1,2,3,5-tetrahydro-s-indaceneHCID 178418339Butyllithium

Product 1

HCID 68747292Dimethyl-(6-methyl-4,8-diphenyl-1,2,3,5-tetrahydro-s-indacenyl)(2-i-propyl-4-(4-t-butylphenyl)-1-indenyl)silane
Yield 72.6%

Reagents, catalysts & solvents 4

HCID 178418260HCID 178418260, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To 11.4 g (35.3 mmol) of 6-methyl-4,8-diphenyl-1,2,3,5-tetrahydro-s-indacene (5c) and 100 mg of copper cyanide (I) in 300 ml of diethylether plus 20 ml of THF was added dropwise at −70° C. 16 ml (40 mmol) of 2.5 M of n-butyllithium in n-hexane. The solution was slowly warmed to room temperature and stirred for 3 hrs at room temperature (yellow brown suspension). Then to the suspension was added at −70° C. 13.4 g (35 mmol) of chloro-(2-i-propyl-4-(4-t-butylphenyl)-indenyl)-dimethylsilane and the solution was warmed to room temperature and stirred over the weekend. The resulting brown slurry solution was poured into an aqueous ammonium chloride solution and the organic layer was washed with brine, dried over sodium sulfate and the solvents were evaporated. The crude product was purified by column chromatography to get 17.0 g of amorphous solid (yield: 64%).

Workup

  1. additionThen to the suspension was added at −70° C
  2. stirringstirred over the weekend
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvents were evaporated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-0cb6aa7d933944998a2e0d691ed1e18e
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07452949B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes