반응 #45539

반응 방정식

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

fluorene

hydrochloric acid

n-butyl lithium hexane

→

aimed compound

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

용매

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
   workup.STIRRINGstirred
3. 3
   온도under reflux for several days
4. 4
   기타set in an ice bath
5. 5
   workup.STIRRINGstirred briefly
6. 6
   기타to separate an organic phase
7. 7
   세척The organic phase was washed with a saturated sodium bicarbonate aqueous solution, water and saturated brine
8. 8
   건조The organic phase was dried with anhydrous magnesium sulfate
9. 9
   여과the drying agent was filtered off
10. 10
    workup.DISTILLATIONthe solvent was distilled off from the filtrate under reduced pressure
11. 11
    기타to give a red solid
12. 12
    기타The solid was purified with a column chromatography
13. 13
    workup.DISTILLATIONthe developing solvent was distilled off under reduced pressure
14. 14
    기타Thereafter, the remaining product was re-crystallized
15. 15
    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, 1.42 g of fluorene (8.52 mmol) was dissolved in 60 ml of dehydrated diethyl ether in a nitrogen atmosphere. To the solution, 5.6 ml of n-butyl lithium/hexane solution (1.58M: 8.85 mmol) was gradually added dropwise in an ice bath and stirred at room temperature over night. To the reaction solution, 2.99 g of 3-tert-butyl-1-methyl-6,6-di(4-chloro-phenyl)fulvene (8.08 mmol) was added and stirred under reflux for several days. The reaction mixture was gradually added dropwise to 30 ml of a hydrochloric acid aqueous solution (1N) set in an ice bath, and stirred briefly. Therein, diethyl ether was added to separate an organic phase. The organic phase was washed with a saturated sodium bicarbonate aqueous solution, 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 red solid. The solid was purified with a column chromatography using 180 g of silica gel (developing solvent: n-hexane) and the developing solvent was distilled off under reduced pressure. Thereafter, the remaining product was re-crystallized using hexane and dried under reduced pressure, and thereby the aimed compound was obtained in an amount of 1.69 g (3.16 mmol) as a pale yellow solid (yield: 39%).

출처