Reaktion #1121734

Reaktionsgleichung

linoleyl methanesulfonate

1-(tert-butyldimethylsilyloxy)-3-(dimethylamino)propan-2-ol

NaH

→

3-(tert-butyldimethylsilyloxy)-N,N-dimethyl-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-amine

Ausbeute 53.0%

Lösungsmittel

toluene

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was then stirred for 18 hours at 90° C
2. 2
   Sonstigequenched by the slow addition of ethanol (10 mL)
3. 3
   EinengenThe mixture was then concentrated
4. 4
   Extraktionextracted three times with EtOAc (20 mL)
5. 5
   WaschenThe combined organic extracts were washed with deionized water (15 mL)
6. 6
   Trocknendried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeChromatographic purification of the residue (0-5% MeOH in chloroform)

Vorschrift

A toluene (10 mL) solution of crude 1-(tert-butyldimethylsilyloxy)-3-(dimethylamino)propan-2-ol (1.0 g, 4.29 mmol, 1.0 equiv) was carefully added dropwise to a toluene suspension (5 mL) of NaH (60%, 0.17 g, 4.29 mmol, 1.0 equiv) at 0° C. under argon and the resultant was stirred for 15 minutes. A toluene solution (5 mL) of linoleyl methanesulfonate (1.47 g, 4.29 mmol, 1.0 equiv) was added dropwise to the stirring mixture and the reaction was then stirred for 18 hours at 90° C. The mixture was then cooled to room temperature and quenched by the slow addition of ethanol (10 mL). The mixture was then concentrated and the residue was taken up with deionized water (15 mL) and extracted three times with EtOAc (20 mL). The combined organic extracts were washed with deionized water (15 mL), dried (MgSO4), filtered, and concentrated. Chromatographic purification of the residue (0-5% MeOH in chloroform) yielded 109 mg (53% yield) of 3-(tert-butyldimethylsilyloxy)-N,N-dimethyl-2-((9Z,12Z)-octadeca-9,12-dienyloxy)propan-1-amine, a thick clear oil.

Quelle