Potassium Carbonate → Ethyl 2-[(4-oxo-3-phenyl-4H-chromen-7-yl)oxy]propionate

HRID 236341

Reaktionsgleichung

Reaktionsgleichung von HRID 236341
[OH:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][O:9][C:4]=2[CH:3]=1.Br[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:24]([O:23][C:21]([CH:20]([O:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][O:9][C:4]=2[CH:3]=1)[CH3:26])=[O:22])[CH3:25]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 53768917-Hydroxyisoflavone

Produkt 1

HCID 3579826Ethyl 2-[(4-oxo-3-phenyl-4H-chromen-7-yl)oxy]propionateAusbeute 181,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 40 g of 7-hydroxy-3-phenyl-4H-1-benzopyran-4-one, 46 g of ethyl 2-bromopropionate, 250 ml of dimethylformamide and 46.5 g of potassium carbonate was stirred well with heating at 80° C. for 2 hours and poured into 270 ml of ice water. The resulting crystalline precipitate was collected by filtration and recrystallized from ethyl acetate-ethanol to give 103 g of 7-(1-ethoxycarbonylethyl)oxy-3-phenyl-4H-1-benzopyran-4-one as white crystals. m.p. 165°-166° C.

Aufarbeitung

  1. filtrationThe resulting crystalline precipitate was collected by filtration
  2. customrecrystallized from ethyl acetate-ethanol

Quellen und Nachweise

ORD-Eintrag
ord-23d214a5cf28460687112731cb37a5d4
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04644012

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