Реакция #1563893

Уравнение реакции

11,14-Eicosadienoic acid

N,O-Dimethylhydroxylamine hydrochloride

HOAt

Et3N

EDC

→

11,14-eicosadienamide

Выход 93.0%

Растворители

DCM

Условия реакции

Обработка

1. 1
   ДругоеReaction
2. 2
   Промывкаwas then washed 5×700 mL water
3. 3
   Промывкаwashed 1×600 mL 1 M NaOH
4. 4
   Сушкаdried with sodium sulfate
5. 5
   Фильтрацияfiltered through celite
6. 6
   Другоеevaporated

Методика

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).

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