Chlorotrimethylsilane → 1,3-Bis(trimethylsilyl)-2-methylindene

HRID 565614

Reaktionsgleichung

Reaktionsgleichung von HRID 565614
C([Li])CCC.[CH3:6][C:7]1[CH2:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.[CH3:16][Si:17](Cl)([CH3:19])[CH3:18]>CCCCCC>[CH3:16][Si:17]([CH3:19])([CH3:18])[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]([Si:17]([CH3:19])([CH3:18])[CH3:16])=[C:7]1[CH3:6]

Komponenten

5

Edukt 3

HCID 6397Chlorotrimethylsilane2×HCID 165871H-Indene, 2-methyl-HCID 178418339Butyllithium

Produkt 1

HCID 212572741,3-Bis(trimethylsilyl)-2-methylindeneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel2×

Versuchsvorschrift

500 ml of hexane and 70 ml of butyllithium (as a 2.5 molar solution in hexane) were introduced into a 1000 ml flask. 0.175 mol of 2-methylindene was added dropwise at the ambient temperature; the mixture was stirred for a further 10 hours. 0.18 mol of trimethylsilyl chloride was then added dropwise at room temperature; the mixture was stirred for a further 10 hours. LiCl was filtered off and 70 ml of butyllithium (as a 2.5 molar solution in hexane) were added to the clear filtrate. After further stirring for 10 hours, 0.18 mol of trimethylsilyl chloride was again added and the mixture was stirred for a further 10 hours. LiCl was filtered off and the solvent was removed in vacuo. Compound 54 remained as a colorless oil. Yield: 85% of the theoretical yield.

Aufarbeitung

  1. stirringthe mixture was stirred for a further 10 hours
  2. filtrationLiCl was filtered off
  3. addition70 ml of butyllithium (as a 2.5 molar solution in hexane) were added to the clear filtrate
  4. stirringAfter further stirring for 10 hours
  5. stirringthe mixture was stirred for a further 10 hours
  6. filtrationLiCl was filtered off
  7. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0dceed20e52b4850b04cecbb5dfc709d
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172169B2

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