Dichlorodimethylsilane → chloro(dimethyl)(2-methyl-8H-indeno[2,1-b]thiophen-8-yl)silane

HRID 1868545Notes

Reaction equation

HRID 1868545 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:4]=2[CH:3]=1.[Li]CCCC.[CH3:19][Si:20]([CH3:23])(Cl)[Cl:21]>CCOCC.CCCCCC>[Cl:21][Si:20]([CH3:23])([CH3:19])[CH:7]1[C:5]2[S:6][C:2]([CH3:1])=[CH:3][C:4]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2

Participants

6

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 113213872-methyl-8H-indeno[2,1-b]thiopheneHCID 178418339Butyllithium

Product 1

HCID 58931541chloro(dimethyl)(2-methyl-8H-indeno[2,1-b]thiophen-8-yl)silaneYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

Suspension of 1.86 g (0.01 mol) 2-methyl-8H-indeno[2,1-b]thiophene in 25 mL ether was treated dropwise with 6.25 mL (0.01 mol) of 1.6M BuLi in hexane at −40° C. under stirring. Then the mixture was stirred in additional 3 h. The resulting mixture was treated with 1.20 mL (0.01 mol) of dimethyldichlorosilane in 5 mL of ether at −70° C.; then it was allowed to warm to r.t. and stirred overnight. The solution was isolated and evaporated to give 2.47 g (89%) of the crude product that was used without further purification.

Workup

  1. stirringThen the mixture was stirred in additional 3 h
  2. stirringstirred overnight
  3. customThe solution was isolated
  4. customevaporated

Sources & evidence

ORD record
ord-07988a1822ef4439ac1635cff40b5dbc
Source dataset
uspto-grants-2009_12
Patent number
US07635781B2

Reaction notes

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