Dichlorodimethylsilane → [4,5-Bis(4-methoxyphenyl)thiophen-2-yl](dimethyl)silane

HRID 1388672Notes

Reaction equation

HRID 1388672 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]([CH3:31])(Cl)Cl.CN(C)CCN(C)C.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][C:11]([SiH:28]([CH3:31])[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

8

Reactant 6

HCID 6398DichlorodimethylsilaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 114037172,3-Bis(4-methoxyphenyl)thiopheneHCID 21225700DiisobutylaluminumhydrideHCID 178418339Butyllithium

Product 1

HCID 71429323[4,5-Bis(4-methoxyphenyl)thiophen-2-yl](dimethyl)silane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,3-bis(4-methoxyphenyl)thiophene (5.92 g, 20 mmole) in 100 ml diethyl ether/20 ml toluene was treated with 1.6 M n-butyl lithium (14 ml, 1.12 equiv.) and heated at reflux for 1.5 hours. The reaction mixture was cooled to -76° and cannulated into a solution of dimethyldichlorosilane (4.6 ml, 1.9 equiv.) in 40 ml diethyl ether at -76°. After 2.5 hours, the reaction mixture was treated with a diisobutylaluminum hydride tetramethylethylenediamine complex prepared by addition of tetramethylethylenediamine (9.9 ml, 66 mmole) to 1 M diisobutylaluminum hydride in hexane (66 ml, 66 mmole). The reaction mixture was stirred 2 hours at 0°, recooled to -30° and quenched with saturated aqueous potassium-sodium tartrate.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe reaction mixture was cooled to -76°
  4. additionthe reaction mixture was treated with a diisobutylaluminum hydride tetramethylethylenediamine complex
  5. customrecooled to -30°
  6. customquenched with saturated aqueous potassium-sodium tartrate

Sources & evidence

ORD record
ord-74b01ee4d7be43328cea0ccc1c6caeed
Source dataset
uspto-grants-1984_02
Patent number
US04432974

Reaction notes

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