1,2-Epoxybutane → 6-Carboxy2'-(2-hydroxy-butoxy)-flavone

HRID 26218

Reaktionsgleichung

Reaktionsgleichung von HRID 26218
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])=[CH:9][C:8]2=[O:22])([O:3]C)=[O:2].[O:23]1[CH:25]([CH2:26][CH3:27])[CH2:24]1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:24][CH:25]([OH:23])[CH2:26][CH3:27])=[CH:9][C:8]2=[O:22])([OH:3])=[O:2]

Komponenten

5

Edukt 3

HCID 78341,2-EpoxybutaneHCID 66854Benzyltrimethylammonium hydroxideHCID 124078666-Carbomethoxy-2'-hydroxy-flavone

Produkt 1

HCID 213250166-Carboxy2'-(2-hydroxy-butoxy)-flavoneAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture consisting of 6-carbomethoxy-2'-hydroxy-flavone (10 g), obtained according to the method described in Example 2, and 1,2-epoxy-butane (6 g) and benzyl-trimethylammonium hydroxide (0.5 ml) in dioxane (40 ml) was kept at reflux temperature for 48 hours. After cooling, dilution with water, and extraction with ethylacetate, the organic phase was washed with potassium carbonate 5% and water. The solution was evaporated to dryness, and the resulting product was treated with the stoichiometric quantity of a solution of potassium hydroxide 1% in ethanol 95% at reflux temperature for an hour. After acidification with acetic acid, concentration under vacuum, dilution with water, filtration and double crystallisation from ethanol, 6-carboxy2'-(2-hydroxy-butoxy)-flavone (4.7 g) was obtained.

Aufarbeitung

  1. customobtained
  2. temperatureat reflux temperature for 48 hours
  3. temperatureAfter cooling
  4. extractiondilution with water, and extraction with ethylacetate
  5. washthe organic phase was washed with potassium carbonate 5% and water
  6. customThe solution was evaporated to dryness
  7. additionthe resulting product was treated with the stoichiometric quantity of a solution of potassium hydroxide 1% in ethanol 95%
  8. temperatureat reflux temperature for an hour
  9. concentrationAfter acidification with acetic acid, concentration under vacuum, dilution
  10. filtrationwith water, filtration and double crystallisation from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8698bf11a6e24a6491845b020b8dccb2
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148900

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