반응 #531795

반응 방정식

compound 22

(11-bromoundecyl)tolylether

Sodium azide

→

(11-aminoundecyl)tolylether

용매

THF

acetonitrile

ethyl acetate

반응 조건

후처리

1. 1
   기타29-hour reaction
2. 2
   온도by refluxing
3. 3
   workup.WAITfollowed by 95-hour
4. 4
   기타reaction at room temperature
5. 5
   기타the solid components were removed by filtration
6. 6
   workup.DISTILLATIONThe solvent of the filtrate was then distilled away under reduced pressure, and 0.313 g of a transparent, viscous liquid
7. 7
   기타was obtained
8. 8
   workup.DISTILLATIONdistilled from calcium hydride in a nitrogen atmosphere
9. 9
   온도was cooled in an ice bath
10. 10
    workup.DISSOLUTIONLithium aluminum hydride (0.054 g) was then dissolved in 20 ml of dried THF
11. 11
    workup.ADDITION80 μl of ion-exchange water, 80 of 15 wt % of aqueous potassium hydride solution, and 240 μl of ion-exchange water were added so as
12. 12
    기타the reaction
13. 13
    기타The precipitate generated was removed by filtration
14. 14
    workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure
15. 15
    기타The solid obtained
16. 16
    세척was washed twice with 30 ml of ion-exchange water
17. 17
    기타The organic phase was then collected
18. 18
    기타The desiccant agent was removed by filtration
19. 19
    workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure
20. 20
    기타was obtained

실험 절차

The compound 22 (0.506 g) was dissolved in 50 ml of acetonitrile. Sodium azide (0.395 g) was then added to that, and 29-hour reaction was carried out by refluxing, followed by 95-hour reaction at room temperature. After the resultant was cooled down to room temperature, the solid components were removed by filtration. The solvent of the filtrate was then distilled away under reduced pressure, and 0.313 g of a transparent, viscous liquid was obtained. This liquid was dissolved in 15 ml of THF distilled from calcium hydride in a nitrogen atmosphere, and was cooled in an ice bath. Lithium aluminum hydride (0.054 g) was then dissolved in 20 ml of dried THF, and was dripped. After the resultant was stirred in an ice bath for one hour, 80 μl of ion-exchange water, 80 of 15 wt % of aqueous potassium hydride solution, and 240 μl of ion-exchange water were added so as to stop the reaction. The precipitate generated was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. The solid obtained was then dissolved in ethyl acetate (30 ml), and was washed twice with 30 ml of ion-exchange water. The organic phase was then collected, and was dehydrated with magnesium sulfate. The desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. In this manner, 0.2 g of (11-aminoundecyl)tolylether 23, which was a white solid, was obtained.

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