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

HRID 863738

Reaction equation

HRID 863738 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-e02ca833ae3a4057ba6d19ec1f5852e2
Source dataset
uspto-grants-1996_10
Patent number
US05561093

Linked notes

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