Reaktion #531797

Reaktionsgleichung

11-bromoundecan-1-ol

sodium azide

→

white solid 32

11-aminoundecan-1-ol

Lösungsmittel

acetonitrile

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITfollowed by 18-hour
2. 2
   Sonstigereaction
3. 3
   Temperaturby refluxing
4. 4
   Sonstigethe solid components were removed by filtration
5. 5
   workup.DISTILLATIONThe solvent of the filtrate was distilled away under reduced pressure
6. 6
   Sonstigeto obtain 13.9 g of a transparent, viscous liquid
7. 7
   workup.DISTILLATIONdistilled from calcium hydride in a nitrogen atmosphere
8. 8
   Temperaturwas cooled in an ice bath
9. 9
   TrocknenLithium 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
    SonstigeThe precipitate generated was removed by filtration
13. 13
    workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure
14. 14
    SonstigeAfter 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
    FiltrationThe precipitate generated was collected by filtration

Vorschrift

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.

Quelle