반응 #587138

반응 방정식

3-tert-butyl-1-methyl-6,6-di(4-tert-butyl-phenyl)fulvene

fluorene

water

n-butyl lithium hexane

→

aimed compound

(3-tert-butyl-5-methyl-cyclopentadienyl) (fluorenyl)di(4-tert-butyl-phenyl)methane

용매

diethylether

diethyl ether

diethyl ether

반응 조건

후처리

1. 1
   기타In a 200 ml three-necked flask equipped with a magnetic stirrer chip and three-way cock
2. 2
   기타To the solution, a solution prepared
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGstirred
5. 5
   온도under reflux for 10 days
6. 6
   workup.STIRRINGstirred at room temperature for 11 days
7. 7
   기타to separate an organic phase
8. 8
   세척The organic phase was washed with distilled water and saturated brine
9. 9
   건조The organic phase was dried with anhydrous magnesium sulfate
10. 10
    여과the drying agent was filtered off
11. 11
    workup.DISTILLATIONthe solvent was distilled off from the filtrate under reduced pressure
12. 12
    기타to give a reddish-brown solid
13. 13
    기타The solid was purified with a column chromatography
14. 14
    workup.DISTILLATIONthe developing solvent was distilled off under reduced pressure
15. 15
    기타The remaining product was re-crystallized
16. 16
    기타dried under reduced pressure

실험 절차

In a 200 ml three-necked flask equipped with a magnetic stirrer chip and three-way cock thoroughly purged with nitrogen, 0.653 g of fluorene (3.93 mmol) was dissolved in 50 ml of dehydrated diethylether in a nitrogen atmosphere. To the solution, 2.7 ml of n-butyl lithium/hexane solution (1.58M: 4.27 mmol) was gradually added dropwise in an ice bath and stirred at room temperature over night. To the solution, a solution prepared by dissolving 2.09 g of 3-tert-butyl-1-methyl-6,6-di(4-tert-butyl-phenyl)fulvene (5.06 mmol) in 100 ml of dehydrated diethyl ether was added and stirred under reflux for 10 days and then stirred at room temperature for 11 days. To the reaction mixture, 30 ml of distilled water was gradually added dropwise in an ice bath, and then diethyl ether was added to separate an organic phase. The organic phase was washed with distilled water and saturated brine. The organic phase was dried with anhydrous magnesium sulfate, thereafter the drying agent was filtered off and the solvent was distilled off from the filtrate under reduced pressure to give a reddish-brown solid. The solid was purified with a column chromatography using 150 g of silica gel (developing solvent: n-hexane) and the developing solvent was distilled off under reduced pressure. The remaining product was re-crystallized using hexane and dried under reduced pressure, and thereby the aimed compound was obtained in an amount of 0.439 g (0.758 mmol) as a pale yellow solid (yield: 19%).

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