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

HRID 270986

Reaktionsgleichung

Reaktionsgleichung von HRID 270986
[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].CCCCCC.C([Li])CCC.[C:33]([C:37]1[CH:38]=[CH:39][C:40](=[C:42]([CH3:44])[CH3:43])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34]>CCOCC.O>[C:33]([C:37]1[CH:38]=[CH:39][CH:40]([C:42]([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)([CH3:44])[CH3:43])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34]

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 146882832-tert-Butyl-5-(propan-2-ylidene)cyclopenta-1,3-dieneHCID 178418339Butyllithium

Produkt 1

HCID 1317251212-(3-Tert-butylcyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propaneAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of 1.98 g (7.1 mmol) of 3,6-di-tert-butylfluorene in 40 ml of ether, 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 1.56 g (9.6 mmol) of 3-tert-butyl-6,6-dimethylfulvene in 20 ml of ether was further dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 60 ml of water was added. The separated organic phase was dried over magnesium sulfate and then filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid was purified by column chromatography (silica gel, developing solvent: hexane) to obtain 1.35 g of a light yellow solid (yield: 43%). The analyzed values are given below.

Aufarbeitung

  1. stirringby stirring at room temperature for one night
  2. dry with materialThe separated organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customFrom the filtrate, the solvent was removed under reduced pressure
  5. customto obtain a solid
  6. customThe solid was purified by column chromatography (silica gel, developing solvent: hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b6650b087f9742b3899941e4f6965496
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449533B2

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