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Cyclopentadiene → Dimethyl(2,7-di-tert-butylfluorenyl)cyclopentadienylsilane

HRID 3619
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 3619
C([Li])CCC.[CH:6]1[CH2:10][CH:9]=[CH:8][CH:7]=1.[CH3:11][Si:12]([CH3:35])([C:14]1[C:26]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:23]=3)[C:18]=2[CH:17]=[CH:16][C:15]=1[C:31]([CH3:34])([CH3:33])[CH3:32])Cl>CCCCCC.O=O.O>[CH3:11][Si:12]([CH3:35])([C:14]1[C:26]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:27]([CH3:28])([CH3:29])[CH3:30])[CH:23]=3)[C:18]=2[CH:17]=[CH:16][C:15]=1[C:31]([CH3:34])([CH3:33])[CH3:32])[CH:7]1[CH:6]=[CH:10][CH:9]=[CH:8]1
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Komponenten

7

Edukt 3

HCID 7612CyclopentadieneHCID 22495163Dimethyl(2,7-di-tert-butylfluorenyl)chlorosilaneHCID 178418339Butyllithium

Produkt 1

HCID 131720589Dimethyl(2,7-di-tert-butylfluorenyl)cyclopentadienylsilaneAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel3×
HCID 977
Oxygen
Lösungsmittel
2×
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

8.5 ml (21 mmol) of a 2.5M solution of butyllithium in hexane were added dropwise to 1.4 g (21 mmol) of cyclopentadiene in 45 ml of O2 -free and H2O-free THF at 0° C. under argon and the mixture was stirred for a further 2 hours at room temperature. This solution was subsequently added at room temperature to a solution of 7.9 g (21 mmol) of 2 in 100 ml of O2 -free and H2O-free THF over a period of 2 hours and the mixture was stirred for a further 1 hour at room temperature. 50 ml of H2O were added, the phases were separated and the aqueous phase was further extracted twice with 30 ml of Et2O each time. The combined organic phases were dried (MgSO4) and the solvent was removed in vacuo. After chromatography on 200 g of silica gel (hexane/methylene chloride 20:1), 4.4 g (51%) of 3 were obtained as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred for a further 1 hour at room temperature
  2. customthe phases were separated
  3. extractionthe aqueous phase was further extracted twice with 30 ml of Et2O each time
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2b4ebe9966634e10a9ec36b7cb413dc4
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05733991

Notizen zur Reaktion

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