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

HRID 1922321

Reaktionsgleichung

Reaktionsgleichung von HRID 1922321
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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, by 83-85° C./0.2 mm Hg. Yield 10.7 g (66%).

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 12 hours at ambient temperature
  2. customevaporated to dryness
  3. distillationFractional distillation
  4. customgave yellowish liquid
  5. customby 83-85° C.

Quellen und Nachweise

ORD-Eintrag
ord-c86c913e4cf0472ca99fb4acc2c8e311
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173828B2

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