Reaction #1563893

Reaction equation

11,14-Eicosadienoic acid

N,O-Dimethylhydroxylamine hydrochloride

HOAt

Et3N

EDC

→

11,14-eicosadienamide

Yield 93.0%

Solvents

DCM

Conditions

Workup

1. 1
   OtherReaction
2. 2
   Washwas then washed 5×700 mL water
3. 3
   Washwashed 1×600 mL 1 M NaOH
4. 4
   Dryingdried with sodium sulfate
5. 5
   Filtrationfiltered through celite
6. 6
   Otherevaporated

Procedure

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