Reaktion #65873

Reaktionsgleichung

6-(dimethylamino)fulvene

LiAlH4

n-butyllithium

HCl

fluorene

n-butyllithium

→

(fluorenyl)(cyclopentadienyl)methane

Lösungsmittel

ether

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed 15.5 hours
2. 2
   workup.STIRRINGthe mixture was stirred for 10 minutes
3. 3
   ExtraktionThe aqueous phase was extracted 3 times with 300 mL ether
4. 4
   Sonstigethe ether evaporated
5. 5
   workup.ADDITIONThe solid residue was mixed with pentane
6. 6
   Filtrationfiltered over silica

Vorschrift

A second batch of the cyclopentadienyl-type ligand, (fluorenyl)(cyclopentadienyl)methane was prepared as follows. A solution of 13.7 g (0.0824 moles) fluorene in 200 mL tetrahydrofuran (THF) was treated with (0.0826 moles) n-butyllithium at room temperature. After 14.5 hours, 10.00 g (0.0825 moles) solid 6-(dimethylamino)fulvene were added to the orange-brown solution and the mixture was stirred at room temperature for 8.5 hours. The mixture was then reacted with 6.50 g (0.171 moles) LiAlH4 and refluxed 15.5 hours. Then 0.0032 moles n-butyllithium was added and the mixture was stirred for 10 minutes. The mixture was hydrolysed with 500 g ice, 500 mL ether and 200 mL concentrated HCl. The aqueous phase was extracted 3 times with 300 mL ether. The ether extracts were combined and the ether evaporated. The solid residue was mixed with pentane and filtered over silica. The yield was 5.7 g (fluorenyl)(cyclopentadienyl)methane having a gas chromatographic purity of 98%.

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