Toluene → Dimethyl-bis(2-methyl-1H-inden-1-yl)silane

HRID 1181616Notes

Reaction equation

HRID 1181616 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:18]([Li])[CH2:19][CH2:20]C.[CH3:23][Si:24]([CH3:27])(Cl)Cl>O.C1COCC1>[CH3:23][Si:24]([CH3:27])([CH:18]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:17]=[C:19]1[CH3:20])[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6398DichlorodimethylsilaneHCID 165871H-Indene, 2-methyl-HCID 178418339Butyllithium

Product 1

HCID 4050248Dimethyl-bis(2-methyl-1H-inden-1-yl)silane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

8.0 g (61.4 mmoles) of 2-methylindene are introduced into 175 mL of toluene and 13 mL of THF, and 24.6 mL of n-butyllithium (2.5 M in toluene) are added without interruption at room temperature. After this addition is complete, the mixture is heated to 80° C. and stirred at this temperature for one hour. It is allowed to cool to 40° C., then 3.96 g (30.7 mmoles) of dimethyldichlorosilane are slowly added dropwise. After this addition, the reaction solution is stirred for three hours at 60° C. and then overnight at room temperature. 70 mL of water are added and the phases that form are separated. The organic phase is washed with 100 mL of water, and the aqueous phase is extracted three times with a total of 100 mL of toluene. The combined organic phases are dried over magnesium sulfate. After separation of the magnesium sulfate, the solvent is removed and the residue is purified by column chromatography. The desired product is isolated in a yield of 8.16 g (84%) (purity 99%).

Workup

  1. additionare added without interruption at room temperature
  2. additionAfter this addition
  3. temperatureto cool to 40° C.
  4. additionAfter this addition
  5. stirringthe reaction solution is stirred for three hours at 60° C.
  6. customovernight
  7. customat room temperature
  8. customthe phases that form are separated
  9. washThe organic phase is washed with 100 mL of water
  10. extractionthe aqueous phase is extracted three times with a total of 100 mL of toluene
  11. dry with materialThe combined organic phases are dried over magnesium sulfate
  12. customAfter separation of the magnesium sulfate
  13. customthe solvent is removed
  14. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-fac146bb6a2a488e83863c65a79b10f1
Source dataset
uspto-grants-2007_10
Patent number
US07285608B2

Reaction notes

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