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Acetone → 7-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid p-benzoylaminophenyl ester

HRID 1105643
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1105643
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1.CC(C)=O.ClC(OCC(C)C)=O.[C:29]([NH:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>N1C=CC=CC=1.C(N(CC)CC)C>[C:29]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:4]2[C:5](=[O:7])[CH2:6][CH:2]([OH:1])[CH:3]=2)=[CH:40][CH:39]=1)(=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 62365Isobutyl chloroformateHCID 459327Benzamide, N-(4-hydroxyphenyl)-HCID 3690897ACMC-20apjz

Produkt 1

HCID 571537857-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid p-benzoylaminophenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049
Pyridine
Lösungsmittel
HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

0.326 g. of 7-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid were dissolved in 20 ml. of dry acetone. At -20° C., 0.23 ml. of triehtylamine were added and then 0.216 ml. isobutyl chloroformate. After 5 minutes, the temperature was permitted to increase to 25° C., and 0.4 g. of p-benzoylaminophenol dissolved in 10 ml. of dry pyridine was added dropwise. After 2 hours, the solvent was distilled off; the residue was extracted in ethyl acetate; the organic phase was washed with water and dried over sodium sulphate. The solvent was distilled off. After chromatographic purification of the residue (silica gel/ethyl acetate), 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid p-benzoylaminophenyl ester (m.p. 168°-169° C.) was obtained.

Aufarbeitung

  1. customAt -20° C.
  2. waitAfter 2 hours
  3. distillationthe solvent was distilled off
  4. extractionthe residue was extracted in ethyl acetate
  5. washthe organic phase was washed with water
  6. dry with materialdried over sodium sulphate
  7. distillationThe solvent was distilled off
  8. customAfter chromatographic purification of the residue (silica gel/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1f90fd7d2f6f452a9a05e11f7cf6d1af
Quelldatensatz
uspto-grants-1982_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04309441

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