Réaction #1563893

Équation de réaction

11,14-Eicosadienoic acid

N,O-Dimethylhydroxylamine hydrochloride

HOAt

Et3N

EDC

→

11,14-eicosadienamide

Rendement 93.0%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   AutreReaction
2. 2
   Lavagewas then washed 5×700 mL water
3. 3
   Lavagewashed 1×600 mL 1 M NaOH
4. 4
   Séchagedried with sodium sulfate
5. 5
   Filtrationfiltered through celite
6. 6
   Autreevaporated

Mode opératoire

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).

Source