Toluene → Bis[2-(cyclohexylmethyl)-4-(4-tert-butylphenyl)-1,5,6,7-tetrahydro-s-indacen-1-yl](dimethyl)silane

HRID 1427717Notes

Reaction equation

HRID 1427717 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:22]3[CH2:21][C:20]([CH2:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:19][C:18]=3[CH:17]=[C:16]3[C:12]=2[CH2:13][CH2:14][CH2:15]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Li][CH2:38][CH2:39][CH2:40][CH3:41].Cl[Si:43](Cl)([CH3:45])[CH3:44]>O.C1COCC1>[CH:24]1([CH2:23][C:20]2[CH:19]([Si:43]([CH:38]3[C:35]4[C:30](=[C:31]([C:8]5[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=5)[C:32]5[CH2:16][CH2:15][CH2:14][C:33]=5[CH:34]=4)[CH:36]=[C:39]3[CH2:40][CH:41]3[CH2:18][CH2:22][CH2:11][CH2:12][CH2:13]3)([CH3:45])[CH3:44])[C:18]3[C:22]([CH:21]=2)=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=2)[C:12]2[CH2:13][CH2:14][CH2:15][C:16]=2[CH:17]=3)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6398DichlorodimethylsilaneHCID 866937974-(4-tert-Butylphenyl)-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indaceneHCID 178418339Butyllithium

Product 1

HCID 66615596Bis[2-(cyclohexylmethyl)-4-(4-tert-butylphenyl)-1,5,6,7-tetrahydro-s-indacen-1-yl](dimethyl)silane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 20.8 g (54.1 mmol) of 4-(4-tert-butylphenyl)-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene in 600 ml of toluene 21.7 ml (54.2 mmol) of 2.5 M nBuLi in hexanes was added dropwise at 20° C. Then, 30 ml of THF was added, and the resulting mixture was stirred for 1 h at 70° C. The resulting mixture was cooled to 0° C., and 3.30 ml (3.49 g, 27.1 mmol) of dichlorodimethylsilane was added. This mixture was stirred for 12 h at room temperature, then 5 ml of water was added, and organic solvents were evaporated using Rotavapor. The product was extracted from the residue by 3×100 ml of dichloromethane. The organic extract was dried over Na2SO4 and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: hexanes and then hexanes-dichloromethane, 10:1, vol.). Yield 15.2 g (68%).

Workup

  1. temperatureThe resulting mixture was cooled to 0° C.
  2. stirringThis mixture was stirred for 12 h at room temperature
  3. customorganic solvents were evaporated
  4. extractionThe product was extracted from the residue by 3×100 ml of dichloromethane
  5. extractionThe organic extract
  6. dry with materialwas dried over Na2SO4
  7. customevaporated to dryness
  8. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent

Sources & evidence

ORD record
ord-b759368d94fb4cf596329290ff471257
Source dataset
uspto-grants-2015_01
Patent number
US08933256B2

Reaction notes

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