Réaction #1121726

Équation de réaction

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

Rendement 53.0%

Solvants

toluene

toluene

toluene

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source