Dichlorodimethylsilane → Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane

HRID 1037712Notes

Reaction equation

HRID 1037712 reaction equation
[CH3:1][CH:2]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[CH:4]=[C:3]1[CH3:10].CC1C2C=CSC=2CC=1C.[Li]CCCC.[Cl:26][Si:27](Cl)([CH3:29])[CH3:28]>C1COCC1>[Cl:26][Si:27]([CH:4]1[C:5]2[S:6][CH:7]=[CH:8][C:9]=2[C:2]([CH3:1])=[C:3]1[CH3:10])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 6398DichlorodimethylsilaneHCID 123075884,5-dimethyl-4H-cyclopenta[b]thiopheneHCID 668093064,5-dimethyl-6H-cyclopenta[b]thiopheneHCID 178418339Butyllithium

Product 1

HCID 58526148Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, to a solution of 10.0 g (66.6 mmol) of a mixture of 4,5-dimethyl-4H-cyclopenta[b]thiophene and 4,5-dimethyl-6H-cyclopenta[b]thiophene in 150 ml of THF, 26.6 ml of 2.5 M (66.6 mmol) nBuLi in hexanes was added dropwise over 30 minutes at −60° C. This mixture was additionally stirred for 2 hours at room temperature and then added dropwise for 3 hours to a solution of 23.7 ml (25.2 g, 200 mmol) of dichlorodimethylsilane in 50 ml of THF. The resulting mixture was stirred for 12 hours at ambient temperature and then evaporated to dryness. Fractional distillation gave yellowish liquid, bp 83-85° C./0.2 mm Hg. Yield 10.7 g (66%).

Workup

  1. stirringThe resulting mixture was stirred for 12 hours at ambient temperature
  2. customevaporated to dryness
  3. distillationFractional distillation
  4. customgave yellowish liquid, bp 83-85° C./0.2 mm Hg

Sources & evidence

ORD record
ord-77d263a97fae40958d9657850a6788c1
Source dataset
uspto-grants-2013_10
Patent number
US08546595B2

Reaction notes

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