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

HRID 2226196Notes

Reaction equation

HRID 2226196 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 a reaction vessel made of glass, 4.3 g (33 mmol) of 2-methylindene was dissolved in 80 ml of tetrahydrofuran, and 21 ml of a 1.6M hexane solution of n-butyllithium was gradually added dropwise to the solution while cooling. The mixture was stirred at room temperature for 1 hour, and then cooled again. To this mixture, 2.1 g of dimethyldichlorosilane was gradually added dropwise, and the mixture was stirred at room temperature for 12 hours. Thereafter, 50 ml of water was added. An organic layer was separated, and dried, thereby giving 3.5 g of dimethylbis(2-methylindenyl)silane.

Workup

  1. temperaturewhile cooling
  2. temperaturecooled again
  3. stirringthe mixture was stirred at room temperature for 12 hours
  4. customAn organic layer was separated
  5. customdried

Sources & evidence

ORD record
ord-863df541633848158fbf1c9d3cd58b4c
Source dataset
uspto-grants-1994_09
Patent number
US05346925

Reaction notes

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