Réaction #969840

Équation de réaction

1,11-diazido-3,6,9-trioxaundecane

hydrochloric acid

triphenylphosphine

→

yellow oil

Rendement 88.0%

11-Azido-3,6,9-trioxaundecanamine

Rendement 88.0%

Solvants

ether

Conditions de réaction

Traitement

1. 1
   AutreThe phases were separated
2. 2
   Extractionthe aqueous phase was extracted with dichloromethane (3×40 ml)
3. 3
   TempératureThe aqueous phase was cooled in an ice/water bath
4. 4
   workup.ADDITIONby addition of KOH
5. 5
   ExtractionThe product was extracted into dichloromethane (5×50 ml)
6. 6
   SéchageCombined organic phases were dried (MgSO4)
7. 7
   FiltrationFiltration and evaporation

Mode opératoire

To a mechanically, vigorously stirred suspension of 1,11-diazido-3,6,9-trioxaundecane (20.8 g, 0.085 mol) in 5%/o hydrochloric acid (200 ml) was added a solution of triphenylphosphine (19.9 g, 0.073 mol) in ether (150 ml) over 3 hrs at room temperature. The reaction mixture was stirred for additional 24 hrs. The phases were separated and the aqueous phase was extracted with dichloromethane (3×40 ml). The aqueous phase was cooled in an ice/water bath and pH was adjusted to ca 12 by addition of KOH. The product was extracted into dichloromethane (5×50 ml). Combined organic phases were dried (MgSO4). Filtration and evaporation gave 14.0 g (88%) of yellow oil. Analysis by MALDI-TOF mass spectroscopy (matrix: α-cyano-4-hydroxycinnamic acid) gave a M+H peak at 219 as expected. Further characterisation using 1H (500 MHz) and 13C (125 MHz) NMR spectroscopy verified the structure.

Source