반응 #587137

반응 방정식

4,4′-di-tert-butyl-benzophenone

potassium hydroxide

hydrochloric acid

3-tert-butyl-1-methyl-cyclopentadiene

→

aimed compound

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

용매

Diethyl ether

dimethoxyethane

dimethoxy ethane

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.ADDITIONwere added in a nitrogen atmosphere
3. 3
   온도under reflux for 1 hr
4. 4
   기타Thereafter, a solution prepared
5. 5
   workup.ADDITIONwas gradually added dropwise
6. 6
   workup.STIRRINGstirred
7. 7
   온도under reflux for 2 days
8. 8
   workup.ADDITIONwas gradually added dropwise in an ice bath
9. 9
   workup.STIRRINGstirred at room temperature for some time
10. 10
    기타to separate an organic phase
11. 11
    세척The organic phase was washed with a saturated sodium bicarbonate aqueous solution, water and saturated brine
12. 12
    건조The organic phase was dried with anhydrous magnesium sulfate
13. 13
    여과the drying agent was filtered off
14. 14
    workup.DISTILLATIONthe solvent was distilled off from the filtrate under reduced pressure
15. 15
    기타to give a reddish-brown solid
16. 16
    기타The solid was purified with a column chromatography
17. 17
    workup.DISTILLATIONthe developing solvent was distilled off 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, 1.58 g of powdery potassium hydroxide (28.2 mmol) and 100 ml of dehydrated dimethoxy ethane were added in a nitrogen atmosphere. To the suspension, 2.31 g of 3-tert-butyl-1-methyl-cyclopentadiene (17.0 mmol) was gradually added dropwise at room temperature and stirred under reflux for 1 hr. Thereafter, a solution prepared by dissolving 5.25 g of 4,4′-di-tert-butyl-benzophenone (17.8 mmol) to 40 ml of dehydrated dimethoxyethane was gradually added dropwise and stirred under reflux for 2 days. To the resulting reaction mixture, 50 ml of a hydrochloric acid aqueous solution (1N) was gradually added dropwise in an ice bath and stirred at room temperature for some time. Diethyl ether was added to the mixed solution 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 reddish-brown solid. The solid was purified with a column chromatography using 240 g of silica gel (developing solvent: n-hexane) and the developing solvent was distilled off under reduced pressure, and thereby the aimed compound was obtained in an amount of 2.10 g (5.09 mmol) as a reddish-orange solid (yield: 30%).

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