Reaktion #834160

Reaktionsgleichung

6,6-di-p-tolyl fulvene

ammonium chloride

2,7-di-tert-butylfluorene

n-butyllithium

→

(2,7-di-tert-butylfluorenyl)cyclopentadienyl di-p-tolyl methane

Ausbeute 67.5%

Lösungsmittel

tetrahydrofuran

diethyl ether

tetrahydrofuran

water

n-hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 300 ml two-necked flask equipped with a magnetic stirrer
2. 2
   Sonstigea three-way cock and a dropping funnel, was purged thoroughly with nitrogen
3. 3
   workup.ADDITIONwas further added
4. 4
   TemperaturWith cooling in an ice bath
5. 5
   Sonstigeto obtain a solution
6. 6
   TemperaturWith the flask cooled in a dry ice/methanol bath
7. 7
   TemperaturThe liquid temperature was gradually raised to room temperature
8. 8
   workup.STIRRINGthe contents were stirred in a nitrogen atmosphere at the temperature for 18 hours
9. 9
   Sonstigeto obtain a solution
10. 10
    workup.ADDITIONThe resulting two-phase solution was poured into a 300 ml separation funnel
11. 11
    Sonstigewas removed
12. 12
    WaschenThe obtained organic phase was washed three times with water 100 ml
13. 13
    Trocknenonce with a saturated salt solution 100 ml, and dried over anhydrous magnesium sulfate
14. 14
    FiltrationThe solution was filtered
15. 15
    Sonstigeto remove solids
16. 16
    workup.DISTILLATIONthe solvent of the filtrate was distilled away
17. 17
    WaschenThe resultant solid was washed with n-hexane

Vorschrift

A 300 ml two-necked flask equipped with a magnetic stirrer, a three-way cock and a dropping funnel, was purged thoroughly with nitrogen. 2,7-di-tert-butylfluorene 1.58 g (5.66 mmol) was placed in the flask, and dehydrated tetrahydrofuran 40 ml was further added. With cooling in an ice bath, 1.56 mol/L n-hexane solution of n-butyllithium, 3.8 ml (5.9 mmol), was dropwise added. The contents were stirred at room temperature in a nitrogen atmosphere for 6.5 hours to obtain a solution. With the flask cooled in a dry ice/methanol bath, a solution of 6,6-di-p-tolyl fulvene 1.76 g (6.82 mmol) in 20 ml of dehydrated tetrahydrofuran, was dropwise added to the flask over a period of 20 minutes by means of the dropping funnel. The liquid temperature was gradually raised to room temperature, and the contents were stirred in a nitrogen atmosphere at the temperature for 18 hours to obtain a solution. A saturated aqueous solution of ammonium chloride 100 ml and diethyl ether 100 ml were gradually added in this order. The resulting two-phase solution was poured into a 300 ml separation funnel, and the funnel was shaken several times so that the water phase was removed. The obtained organic phase was washed three times with water 100 ml and once with a saturated salt solution 100 ml, and dried over anhydrous magnesium sulfate. The solution was filtered to remove solids, and the solvent of the filtrate was distilled away. The resultant solid was washed with n-hexane to obtain 2.05 g of (2,7-di-tert-butylfluorenyl)cyclopentadienyl di-p-tolyl methane as a white solid (3.82 mmol, 67.5% yield). Identification of the (2,7-di-tert-butylfluorenyl)cyclopentadienyl di-p-tolyl methane was made by 1H NMR and the FD-mass spectrometric analysis, the results being given below:

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