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

HRID 1857066Notes

Reaction equation

HRID 1857066 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.[CH3:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:17]([Li])[CH2:18][CH2:19]C.[CH3:22][Si:23]([CH3:26])(Cl)Cl.O1CCC[CH2:28]1>O>[CH3:22][Si:23]([CH3:26])([CH:13]1[C:12]2[C:16](=[CH:17][CH:18]=[CH:19][CH:11]=2)[CH:15]=[C:14]1[CH3:28])[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 5

HCID 6398DichlorodimethylsilaneHCID 8028TetrahydrofuranHCID 8058HexaneHCID 165871H-Indene, 2-methyl-HCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 500-ml glass reaction vessel, 4.3 g (33 mmol) of 2-methylindene was dissolved in 80 ml of tetrahydrofuran. 21 ml of a 1.6 M hexane solution of n-butyllithium was slowly added dropwise to the reaction vessel while cooling. The mixture was stirred at room temperature for one hour, and then cooled again. To this mixture, 2.1 g of dimethyldichlorosilane was slowly added dropwise, and the resulting mixture was stirred at room temperature for 12 hours. 50 ml of water was added to the mixture, and the organic phase was fractionated and dried to give 3.5 g of dimethylbis-(2-methylindenyl) silane.

Workup

  1. temperaturewhile cooling
  2. temperaturecooled again
  3. stirringthe resulting mixture was stirred at room temperature for 12 hours
  4. customdried

Sources & evidence

ORD record
ord-d90f5836e8b14c32b18e19e9f5dce369
Source dataset
uspto-grants-2000_11
Patent number
US06143911

Reaction notes

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