Reaktion #82857

Reaktionsgleichung

3-(dimethylamino)-1,2-propanediol

potassium tert-butoxide

oleyl toluenesulfonate

→

title compound

Ausbeute 72.6%

N-(2,3-Di-(9-(Z)-octadecenyloxy))prop-1-yl-N,N,-dimethylamine

Ausbeute 72.6%

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn accordance with Reaction Scheme I
2. 2
   TemperaturThe mixture was heated to 50° C.
3. 3
   workup.STIRRINGstirred for an additional 0.25 hour
4. 4
   SonstigeThe vacuum was removed
5. 5
   workup.ADDITIONthe reaction vessel was filled with nitrogen gas to room pressure (approx. 1 atm.)
6. 6
   TemperaturThe temperature was increased until the reaction
7. 7
   Sonstige(approximately 140° C.)
8. 8
   workup.STIRRINGthe mixture was stirred
9. 9
   Temperaturat reflux for 3 hours
10. 10
    workup.ADDITIONThe mixture was diluted with hexane (100 ml)
11. 11
    Extraktionextracted with water (2×50 ml)
12. 12
    EinengenThe organic layer was concentrated
13. 13
    Wascheneluted with the same solvent mixture

Vorschrift

In accordance with Reaction Scheme I, a mixture of 3-(dimethylamino)-1,2-propanediol (1.19 g, 10 mmol), potassium tert-butoxide (3.36 g, 30 mmol) and oleyl toluenesulfonate (12.7 g, 30 mmol) in xylenes (50 ml) was stirred at room temperature under house vacuum (approx. 30 torr) for 0.5 hour. The mixture was heated to 50° C. and stirred for an additional 0.25 hour. The vacuum was removed and the reaction vessel was filled with nitrogen gas to room pressure (approx. 1 atm.). The temperature was increased until the reaction boiled (approximately 140° C.) and the mixture was stirred at reflux for 3 hours. The mixture was diluted with hexane (100 ml) and extracted with water (2×50 ml). The organic layer was concentrated, applied to a column of silica gel (150 g) packed in hexanes in ether (1:2), then eluted with the same solvent mixture to give the title compound (4.5 g) as an oil.

Quelle