Ethyl Acrylate → HCID 86682233, compound

HRID 1479324Notes

Reaction equation

HRID 1479324 reaction equation
[CH2:1]([O:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:44]([O:48][CH2:49][CH3:50])(=[O:47])[CH:45]=[CH2:46].[O-]CC.[Na+]>C(O)C>[CH2:26]([O:25][CH2:24][CH2:23][N:22]([CH2:21][CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:46][CH2:45][C:44]([O:48][CH2:49][CH3:50])=[O:47])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 2723922Sodium ethoxideHCID 86682234HCID 86682234, compound

Product 1

HCID 86682233HCID 86682233, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 67 (400 mg, 0.660 mmol) obtained in Example 67 was dissolved in ethanol (8 mL), and stirred overnight under heat and reflux after adding ethyl acrylate (3.59 mL, 33.0 mmol) and sodium ethoxide (22.5 mg, 0.330 mmol). After cooling the reaction solution, the solvent was distilled away under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 98/2) to give ethyl 3-(bis(2-((Z)-octadec-9-enyloxy)ethyl)amino)propanoate (399 mg, 85.6%).

Workup

  1. temperatureunder heat
  2. temperaturereflux
  3. temperatureAfter cooling the reaction solution
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 98/2)

Sources & evidence

ORD record
ord-b03f16ab19d64cf38172e5114c6c8c3f
Source dataset
uspto-grants-2016_08
Patent number
US09408914B2

Reaction notes

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