Water → Ethyl 5-(p-heptyloxybenzyloxy)-1-methoxy-2-indaneacetate

HRID 1197085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197085
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][CH3:12])[CH:6]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:5]2.[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH:7]([O:11][CH3:12])[CH:6]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:5]3)=[CH:29][CH:28]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14674285p-Heptyloxybenzyl chlorideHCID 54284451Ethyl 5-hydroxy-1-methoxyindane-2-acetate

Produkt 1

HCID 53634688Ethyl 5-(p-heptyloxybenzyloxy)-1-methoxy-2-indaneacetateAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In 2 ml of dimethylformamide were dissolved 190 mg of ethyl 5-hydroxy-1-methoxyindane-2-acetate and 220 mg of p-heptyloxybenzyl chloride. To the solution was added 180 mg of potassium carbonate. The mixture was stirred at 60° C. overnight. After allowing to cool, water and ethyl acetate were added to the mixture. By thoroughly shaking the mixture, the organic layer was separated. After washing with water, drying and concentrating the organic layer, the residue obtained was purified by flash chromatography (eluant: toluene/ethyl acetate (25/1)) to obtain 220 mg of ethyl 5-(p-heptyloxybenzyloxy)-1-methoxy-2-indaneacetate as a colorless oily product.

Aufarbeitung

  1. temperatureto cool
  2. stirringBy thoroughly shaking the mixture
  3. customthe organic layer was separated
  4. washAfter washing with water
  5. customdrying
  6. concentrationconcentrating the organic layer
  7. customthe residue obtained
  8. customwas purified by flash chromatography (eluant: toluene/ethyl acetate (25/1))

Quellen und Nachweise

ORD-Eintrag
ord-f4da7c763aae4062aa13c2f45efe2161
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116853

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