Acetamidomalonic acid diethyl ester → Diethyl 2-acetamido-2-(9-octadecenyl)malonate

HRID 1451570

Reaktionsgleichung

Reaktionsgleichung von HRID 1451570
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[O-]CC.[Na+].[CH2:20](Cl)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(O)C>[C:1]([NH:4][C:5]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 5580461-Chlorooctadec-9-eneHCID 2723922Sodium ethoxide

Produkt 1

HCID 53823167Diethyl 2-acetamido-2-(9-octadecenyl)malonateAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Diethyl 2-acetamidomalonate (15 g) was dissolved in 200 ml of dry ethanol and 5.6 g of sodium ethoxide was added thereto. To the reaction mixture, 22 g of 9-octadecenyl chloride was added while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with ethanol-concentrated hydrochloric acid (11:1) and concentrated. The concentrate was purified by silica gel column chromatography to give 1.3 g of diethyl 2-acetamido-2-(9-octadecenyl)malonate as a colorless, oily and viscous substance.

Aufarbeitung

  1. temperaturethe mixture was refluxed for about 15 hours
  2. concentrationconcentrated
  3. customThe concentrate was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5d7ee4bd5a4f4c78bde0f14534777690
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604229

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