Reaktion #1563893

Reaktionsgleichung

11,14-Eicosadienoic acid

N,O-Dimethylhydroxylamine hydrochloride

HOAt

Et3N

EDC

→

11,14-eicosadienamide

Ausbeute 93.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction
2. 2
   Waschenwas then washed 5×700 mL water
3. 3
   Waschenwashed 1×600 mL 1 M NaOH
4. 4
   Trocknendried with sodium sulfate
5. 5
   Filtrationfiltered through celite
6. 6
   Sonstigeevaporated

Vorschrift

11,14-Eicosadienoic acid, (11Z,14Z)- (50 g, 162 mmol), N,O-Dimethylhydroxylamine hydrochloride (31.6 g, 324 mmol), HOAt (44.1 g, 324 mmol), Et3N (45.2 mL, 324 mmol), and EDC (62.1 g, 324 mmol) were mixed in DCM (810 mL) and stirred overnight at ambient temperature. Reaction was then washed 5×700 mL water, then washed 1×600 mL 1 M NaOH, dried with sodium sulfate, filtered through celite and evaporated to obtain 53.06 g (93%) 11,14-eicosadienamide, N-methoxy-N-methyl-, (11Z,14Z) as a clear golden oil. 1H NMR (400 MHz, CDCl3) δ 5.35 (m, 4H), 3.68 (s, 3H), 3.18 (s, 3H), 2.77 (m, 2H), 2.41 (t, J=7 Hz, 2H), 2.05 (m, 4H), 1.63 (m, 2H), 1.40-1.26 (m, 18H), 0.89 (t, J=7 Hz, 3H).

Quelle