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Hexane → 2-(3-Tert-butylcyclopentadienyl)-3-(3,6-di-tert-butylfluorenyl)pentane

HRID 495762
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 495762
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:12][CH:11]=3)([CH3:4])([CH3:3])[CH3:2].[CH3:22]CCCCC.C([Li])CCC.[C:33]([C:37]1[CH:38]=[CH:39][C:40](=[C:42]([CH2:45]C)[CH2:43][CH3:44])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34]>C1COCC1.CCOCC.O>[C:33]([C:37]1[CH:38]=[CH:39][CH:40]([CH:42]([CH:43]([C:11]2[C:10]3[CH2:9][C:8]4[C:16](=[CH:17][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=4)[C:15]=3[CH:14]=[C:13]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=2)[CH2:44][CH3:22])[CH3:45])[CH:41]=1)([CH3:34])([CH3:35])[CH3:36]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 178181433-Tert-butyl-6,6-diethylfulveneHCID 178418339Butyllithium

Produkt 1

HCID 1317251382-(3-Tert-butylcyclopentadienyl)-3-(3,6-di-tert-butylfluorenyl)pentaneAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1.99 g (7.1 mmol) of 3,6-di-tert-butylfluorene in 30 ml of THF, 4.6 ml (7.5 mmol) of a hexane solution of n-butyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. To the resulting red solution, a solution of 1.50 g (7.9 mmol) of 3-tert-butyl-6,6-diethylfulvene in 30 ml of THF was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 100 ml of ether, 50 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was isolated and purified by column chromatography (silica gel, developing solvent: hexane) to obtain 2.34 g (4.99 mmol) of a white solid (yield: 70%). The analyzed values are given below.

Aufarbeitung

  1. stirringby stirring at room temperature for one night
  2. additionwas added
  3. washThe separated organic phase was washed with water
  4. dry with materiala saturated saline solution, then dried over magnesium sulfate
  5. filtrationfiltered
  6. customFrom the filtrate, the solvent was removed under reduced pressure
  7. customto obtain a liquid
  8. customThe liquid was isolated
  9. custompurified by column chromatography (silica gel, developing solvent: hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f5874959c87c48bd90b0eceeb9bf4a08
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06939928B1

Notizen zur Reaktion

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