Réaction #324363

Équation de réaction

3-(dimethylamino)-1,2-propanediol

EDCI

EtOAc

linoleic acid

→

ester

Octadeca-9,12-dienoic acid 3-dimethylamino-2-octadeca-9,12-dienoyloxy-propyl ester

Solvants

—

hexanes

DMF

diisopropyl ethylamine

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   Autrethe completion of the reaction
3. 3
   Extractionextracted with ethyl acetate (2×100 mL)
4. 4
   LavageThe combined organic layers were washed with water (100 mL), saturated NaHCO3 (100 mL)
5. 5
   Séchagedried over Na2SO4
6. 6
   AutreConcentration of the organic layer provided the crude product which
7. 7
   Autrewas purified by column chromatography (silica gel, eluent: 20% EtOAc in hexanes)
8. 8
   workup.ADDITIONThe fractions containing pure product
9. 9
   Concentrationconcentrated

Mode opératoire

To a solution of the linoleic acid (25 g, 89.1 mmol) in anhydrous DMF (60 mL), diisopropyl ethylamine (17 mL, 100 mml) was added at room temperature with stirring followed by 3-(dimethylamino)-1,2-propanediol (4.8 g, 40.5 mmol) and EDCI (17.25 g, 89.9 mmol) and the mixture was stirred at room temperature overnight. The TLC of the reaction mixture (eluent 20% EtOAc in hexanes) showed the completion of the reaction. The reaction mixture was poured into ice water and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water (100 mL), saturated NaHCO3 (100 mL) and dried over Na2SO4. Concentration of the organic layer provided the crude product which was purified by column chromatography (silica gel, eluent: 20% EtOAc in hexanes). The fractions containing pure product was pooled and concentrated. The pure ester was isolated as a clear liquid (5.7 g, 22%). MS m/z 645 (M+H). 1H NMR CDCl3 δ 0.88 (t, J=6.3 Hz, 6H), 1.20-1.39 (m, 28H), 1.61 (t, J=4.9 Hz, 12H), 2.03-2.08 (m, 8H), 2.26-2.38 (m, 10H), 2.44-2.56 (m, 2H), 2.76 (t, J=6.3 Hz, 4H), 4.09 (dd, J=6.1 Hz & 11.9 Hz, 1H), 4.36 (dd, J=3.3 & 11.9 Hz, 1H), 5.29-5.34 (m, 1H), 5.34-5.41 (m, 8H). 13C NMR CDCl3 δ 14.30, 22.79, 25.08, 25.10, 25.83, 27.40, 29.26, 29.30, 29.34, 29.42, 29.55, 29.83, 31.73, 34.32, 34.58, 46.01, 59.37, 64.02, 128.08, 128.24, 130.21, 130.42, 173.39, 173.65.

Source