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

HRID 271796Notes

Reaction equation

HRID 271796 reaction equation
[C:1]1([C:7]2[C:18]3[CH2:17][C:16]([CH3:19])=[CH:15][C:14]=3[CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.Cl[Si:26]([CH:29]1[C:37]2[C:32](=[C:33]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[CH:44]([CH3:46])[CH3:45])([CH3:28])[CH3:27].[Cl-].[NH4+]>C(OCC)C.CCCCCC.[Cu](C#N)C#N>[CH3:27][Si:26]([CH3:28])([CH:11]1[C:12]2[C:8](=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:18]3[CH2:17][C:16]([CH3:19])=[CH:15][C:14]=3[CH:13]=2)[CH2:9][CH2:10]1)[CH:29]1[C:37]2[C:32](=[C:33]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[CH:44]([CH3:45])[CH3:46]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 534453466-Methyl-4-phenyl-1,2,3,5-tetrahydro-s-indaceneHCID 68744992Chloro-(2-i-propyl-4-phenyl-indenyl)-dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 68745586Dimethyl-(4-phenyl-6-methyl-1,2,3,5-tetrahydro-s-indacenyl)(2-i-propyl-4-phenyl-1-indenyl)-silaneYield 104.3%

Reagents, catalysts & solvents 3

HCID 178418260HCID 178418260, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To 12.3 g (50 mmol) of 4-phenyl-6-methyl-1,2,3,5-tetrahydro-s-indacene (2b) and 150 mg (1.5 mmol) of copper cyanide (I) in 450 ml of diethylether was added dropwise at −70° C. 23 ml (57 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. Then to the solution was added at −70° C. 16.4 g (50 mmol) of chloro-(2-i-propyl-4-phenyl-indenyl)-dimethylsilane and the solution was warmed to room temperature and stirred for 5 hrs. The resulting back 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 to give 28 g of crude product. This was purified by column chromatography (800 g of silica gel, 101 Heptane:CH2Cl2=5:1). Yield: 9.5 g (35%)

Workup

  1. additionThen to the solution was added at −70° C
  2. stirringstirred for 5 hrs
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvents were evaporated

Sources & evidence

ORD record
ord-0655d291149141199cfe92ce5ecfcf50
Source dataset
uspto-grants-2008_11
Patent number
US07452949B2

Reaction notes

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