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Hydrochloric Acid → 2-(2-(2-Benzyloxyphenyl)ethyl)-2-ethoxycarbonylpentanoic acid

HRID 617584
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 617584
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([CH2:28][CH2:29][CH3:30])([C:23]([O:25]CC)=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:28][CH2:29][CH3:30])[C:23]([OH:25])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22618813Diethyl 2-(2-(2-benzyloxyphenyl)ethyl)-2-propylmalonate

Produkt 1

HCID 226188042-(2-(2-Benzyloxyphenyl)ethyl)-2-ethoxycarbonylpentanoic acidAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

To a solution of diethyl 2-(2-(2-benzyloxyphenyl)ethyl)-2-propylmalonate (10 g) in ethanol (50 ml), a solution of potassium hydroxide (1.9 g) in ethanol (180 ml) was added and the mixture was refluxed under heating for 6.5 hours. Ethanol (45 ml) was added thereto and the mixture was stirred at room temperature for 4 days. The reaction mixture was poured into a dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; chloroform-methanol=12:1) to give the subject compound (5.7 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 6.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ba729b748e3141bfb51bf486af32ab4e
Quelldatensatz
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05948820

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