反応 #324363

反応方程式

3-(dimethylamino)-1,2-propanediol

EDCI

EtOAc

linoleic acid

→

ester

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

溶媒

—

hexanes

DMF

diisopropyl ethylamine

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   その他the completion of the reaction
3. 3
   抽出extracted with ethyl acetate (2×100 mL)
4. 4
   洗浄The combined organic layers were washed with water (100 mL), saturated NaHCO3 (100 mL)
5. 5
   乾燥dried over Na2SO4
6. 6
   その他Concentration of the organic layer provided the crude product which
7. 7
   その他was purified by column chromatography (silica gel, eluent: 20% EtOAc in hexanes)
8. 8
   workup.ADDITIONThe fractions containing pure product
9. 9
   濃縮concentrated

実験手順

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.

出典