Hexane → 2-(3-(1-Ethyl-1-methylpropyl)cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propane

HRID 271001

Reaktionsgleichung

Reaktionsgleichung von HRID 271001
[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.[CH2:33]([C:35]([C:39]1[CH:40]=[CH:41][C:42](=[C:44]([CH3:46])[CH3:45])[CH:43]=1)([CH3:38])[CH2:36][CH3:37])[CH3:34]>C1COCC1.CCOCC.O>[CH2:33]([C:35]([C:39]1[CH:40]=[CH:41][CH:42]([C:44]([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)([CH3:46])[CH3:45])[CH:43]=1)([CH3:38])[CH2:36][CH3:37])[CH3:34]

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 111404373,6-DI-Tert-butylfluoreneHCID 178181393-(1-Ethyl-1-methylpropyl)-6,6-dimethylfulveneHCID 178418339Butyllithium

Produkt 1

HCID 1317251272-(3-(1-Ethyl-1-methylpropyl)cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propaneAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1.93 g (6.9 mmol) of 3,6-di-tert-butylfluorene in 30 ml of THF, 4.7 ml (7.6 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 1.70 g (8.9 mmol) of 3-(1-ethyl-1-methylpropyl)-6,6-dimethylfulvene in 10 ml of THF was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for 5 days. 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 1.20 g (2.56 mmol) of a white solid (yield: 37%). The analyzed values are given below.

Aufarbeitung

  1. stirringby stirring at room temperature for 5 days
  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-24954913bc5247dc8eece13dcfd82d44
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449533B2

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