Chlorotrimethylsilane → [4,5-Bis(4-methoxyphenyl)thiophen-2-yl](trimethyl)silane

HRID 1388671Notes

Reaction equation

HRID 1388671 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C([Li])CCC.[CH3:27][Si:28](Cl)([CH3:30])[CH3:29]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][C:11]([Si:28]([CH3:30])([CH3:29])[CH3:27])=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 114037172,3-Bis(4-methoxyphenyl)thiopheneHCID 178418339Butyllithium

Product 1

HCID 13277375[4,5-Bis(4-methoxyphenyl)thiophen-2-yl](trimethyl)silane

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

2,3-Bis(4-methoxyphenyl)thiophene (5.92 g, 20 mmole) was dissolved in 100 ml toluene and the volume reduced by approximately 3/4 by distillation. The cooled solution was diluted with 130 ml diethyl ether, cooled to ~10° and treated with 1.55 M n-butyl lithium (15.5 ml, 1.2 equiv.). The reaction mixture was heated at reflux for 1.5 hours, cooled to 0° and treated dropwise with a solution of trimethylsilyl chloride (3.1 ml, 1.2 equiv.) in 5 ml diethyl ether. The reaction mixture was stirred overnight at room temperature and then quenched with water.

Workup

  1. distillationthe volume reduced by approximately 3/4 by distillation
  2. additionThe cooled solution was diluted with 130 ml diethyl ether
  3. temperaturecooled to ~10°
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 1.5 hours
  6. temperaturecooled to 0°
  7. customquenched with water

Sources & evidence

ORD record
ord-8c651b75d6894f03a5d7ac6ed0088bb6
Source dataset
uspto-grants-1984_02
Patent number
US04432974

Reaction notes

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