반응 #42259

반응 방정식

3-tert-butyl-1-methyl-6,6-diphenyl fulvene

2,7-di-tert-butyl-fluorene

hydrochloric acid

n-butyl lithium hexane

→

aimed compound

(3-tert-butyl-5-methyl-cyclopentadienyl)(2,7-di-tert-butyl-fluorenyl)diphenylmethane

용매

diethyl ether

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 reaction solution, a solution prepared
3. 3
   workup.ADDITIONwas added
4. 4
   workup.STIRRINGstirred
5. 5
   온도with refluxing for 7 days
6. 6
   기타to separate an organic phase
7. 7
   세척The organic phase was washed with a saturated sodium bicarbonate aqueous solution 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 reddish-brown liquid
12. 12
    기타The liquid was purified by a column chromatography
13. 13
    workup.DISTILLATIONthe developing solvent was distilled off under reduced pressure
14. 14
    기타The remainder 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, 2.53 g of 2,7-di-tert-butyl-fluorene (9.10 mmol) was dissolved in 70 ml of dehydrated diethyl ether in a nitrogen atmosphere. To the solution, 6.4 ml of a n-butyl lithium/hexane solution (1.56M: 9.98 mmol) was gradually added dropwise in an ice bath and stirred at room temperature over night. To the reaction solution, a solution prepared by dissolving 3.01 g of 3-tert-butyl-1-methyl-6,6-diphenyl fulvene (10.0 mmol) in 40 ml of dehydrated diethyl ether was added and stirred with refluxing for 7 days. The reaction mixture was added to 100 ml of a hydrochloric acid aqueous solution (1N) and thereafter diethyl ether was added to separate an organic phase. The organic phase was washed with a saturated sodium bicarbonate aqueous solution 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 liquid. The liquid was purified by a column chromatography using 180 g of silica gel (developing solvent: n-hexane) and the developing solvent was distilled off under reduced pressure. The remainder was re-crystallized using methanol and dried under reduced pressure, and thereby the aimed compound was obtained in an amount of 1.65 g (2.85 mmol) as a pale yellow solid (yield: 31%).

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