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Hydrochloric Acid → Diethyl acetamido(3-phenylpropyl)propanedioate

HRID 617832
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 617832
[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].[C:16]1([CH2:22][CH2:23][CH2:24]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>C(O)C>[C:1]([NH:4][C:5]([CH2:24][CH2:23][CH2:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 12503(3-Bromopropyl)benzeneHCID 14041Acetamidomalonic acid diethyl ester

Produkt 1

HCID 21849514Diethyl acetamido(3-phenylpropyl)propanedioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium (0.23 g) was added to 15 ml of absolute ethanol and the mixture was stirred at room temperature for 30 minutes in a nitrogen flow to give a 10 mmol solution of sodium ethoxide in ethanol. To this solution, 1.98 g of diethyl 2-acetamidomalonate was added and the mixture was heated at 50° C. for 30 minutes in a stream of nitrogen. 3-Phenylpropyl bromide was added thereto at room temperature and the mixture was refluxed under heating for 24 hours. The mixture was neutralized with dilute hydrochloric acid and ethanol was distilled away. The resultant residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4-1:1) and recrystallized from diisopropyl ether-hexane to give 800 mg of diethyl 2-acetamido-2-(3-phenylpropyl)malonate as white crystals.

Aufarbeitung

  1. temperatureat room temperature and the mixture was refluxed
  2. temperatureunder heating for 24 hours
  3. distillationwas distilled away
  4. extractionThe resultant residue was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled away
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4-1:1)
  9. customrecrystallized from diisopropyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-918890855d204bffa55a4f00889d2fc2
Quelldatensatz
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05952316

Notizen zur Reaktion

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