Reaktion #54947

Reaktionsgleichung

3-[3-Hydroxy-5-oxo-2-(3-oxo-oct-1-enyl)cyclopent-1-enyl]propanoic acid

triethylamine

→

3-[3-Hydroxy-5-oxo-2-(3-oxo-octan-1-yl)cyclopent-1-enyl]propanoic acid

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe catalyst was removed by filtration
2. 2
   Sonstigethe filtrate rotary evaporated to a crystalline solid
3. 3
   workup.DISSOLUTIONThe solid was dissolved in chloroform
4. 4
   TrocknenAfter drying over anhydrous sodium sulphate the solvent
5. 5
   Sonstigewas removed by rotary evaporation
6. 6
   Sonstigeto yield an oil
7. 7
   SonstigeChromatography on a silicic acid column (Bio Sil A) with chloroform as eluant was effective in purification of the product, 3-[3-hydroxy-5-oxo-2-(3-oxo-octan-1-yl)cyclopent-1-enyl]propanoic acid

Vorschrift

3-[3-Hydroxy-5-oxo-2-(3-oxo-oct-1-enyl)cyclopent-1-enyl]propanoic acid (1.0 g.) was dissolved in absolute ethanol (50 ml.) and triethylamine (5 ml.) and hydrogenated over a Raney Nickel W2 catalyst at room temperature for 80 minutes. The catalyst was removed by filtration and the filtrate rotary evaporated to a crystalline solid. The solid was dissolved in chloroform and shaken with 1 M hydrochloric acid and then with brine. After drying over anhydrous sodium sulphate the solvent was removed by rotary evaporation to yield an oil. Chromatography on a silicic acid column (Bio Sil A) with chloroform as eluant was effective in purification of the product, 3-[3-hydroxy-5-oxo-2-(3-oxo-octan-1-yl)cyclopent-1-enyl]propanoic acid.

Quelle