反応 #531797

反応方程式

11-bromoundecan-1-ol

sodium azide

→

white solid 32

11-aminoundecan-1-ol

溶媒

acetonitrile

THF

反応条件

後処理

1. 1
   workup.WAITfollowed by 18-hour
2. 2
   その他reaction
3. 3
   温度by refluxing
4. 4
   その他the solid components were removed by filtration
5. 5
   workup.DISTILLATIONThe solvent of the filtrate was distilled away under reduced pressure
6. 6
   その他to obtain 13.9 g of a transparent, viscous liquid
7. 7
   workup.DISTILLATIONdistilled from calcium hydride in a nitrogen atmosphere
8. 8
   温度was cooled in an ice bath
9. 9
   乾燥Lithium aluminum hydride (2.53 g) was then dried
10. 10
    workup.DISSOLUTIONwas dissolved in 250 ml of THF
11. 11
    workup.ADDITIONAfter that, 2.5 ml of ion-exchange water, 3.5 ml of 15 wt % aqueous sodium hydride solution, and 7.5 ml of ion-exchange water were added so as
12. 12
    その他The precipitate generated was removed by filtration
13. 13
    workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure
14. 14
    その他After the filtrate was dried under reduced pressure
15. 15
    workup.DISSOLUTIONthe dried filtrate was dissolved in 60 ml of THF
16. 16
    workup.ADDITIONthe same volume of heptane was added to that
17. 17
    ろ過The precipitate generated was collected by filtration

実験手順

11-bromoundecan-1-ol (the compound 31) (15.1 g) was dissolved in 250 ml of acetonitrile, and 15.7 g of sodium azide was added to that, followed by 18-hour reaction caused by refluxing. After cooled down to room temperature, the solid components were removed by filtration. The solvent of the filtrate was distilled away under reduced pressure, to obtain 13.9 g of a transparent, viscous liquid. Of this liquid, 8.34 g was dissolved in 60 ml of THF distilled from calcium hydride in a nitrogen atmosphere, and was cooled in an ice bath. Lithium aluminum hydride (2.53 g) was then dried, and was dissolved in 250 ml of THF. The resultant was dripped, and was then stirred in an ice bath for one hour. After that, 2.5 ml of ion-exchange water, 3.5 ml of 15 wt % aqueous sodium hydride solution, and 7.5 ml of ion-exchange water were added so as to stop reactions. The precipitate generated was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. After the filtrate was dried under reduced pressure, the dried filtrate was dissolved in 60 ml of THF, and the same volume of heptane was added to that. The precipitate generated was collected by filtration, to obtain 5.1 g of a white solid 32.

出典