Ethyl Acrylate → HCID 71292994, compound

HRID 1479315Notes

Reaction equation

HRID 1479315 reaction equation
[CH2:1]([O:19][C@H:20]1[C@H: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]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:23][NH:22][CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH: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>[CH2:1]([O:19][C@H:20]1[C@H: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]/[CH:37]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:23][N:22]([CH2:46][CH2:45][C:44]([O:48][CH2:49][CH3:50])=[O:47])[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 2723922Sodium ethoxideHCID 86699633HCID 86699633, compound

Product 1

HCID 71292994HCID 71292994, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 1 (100 mg, 0.167 mmol) obtained in Example 1 was dissolved in ethanol (2 mL), and stirred for 5.5 hours under heat and reflux after adding ethyl acrylate (0.181 mL, 1.67 mmol) and sodium ethoxide (5.7 mg, 0.083 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 97/3) to give ethyl 3-((3R,4R)-3,4-bis((9Z,12Z)-octadec-9,12-dienyloxy)pyrrolidin-1-yl)propanoate (107 mg, 91.2%).

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 97/3)

Sources & evidence

ORD record
ord-6e98d29dd9a1402bb0e3a7e51f8f3cc1
Source dataset
uspto-grants-2016_08
Patent number
US09408914B2

Reaction notes

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