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

HRID 26669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 26669
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[C:3]1[CH:13]=[CH:14][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(N(CC)CC)C>C(O)C.[Ni]>[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[C:3]1[CH2:13][CH2:14][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Komponenten

5

Edukt 2

HCID 8471TriethylamineHCID 70603560HCID 70603560, Verbindung

Produkt 1

HCID 213220713-[3-Hydroxy-5-oxo-2-(3-oxo-octan-1-yl)cyclopent-1-enyl]propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe filtrate rotary evaporated to a crystalline solid
  3. dissolutionThe solid was dissolved in chloroform
  4. dry with materialAfter drying over anhydrous sodium sulphate the solvent
  5. customwas removed by rotary evaporation
  6. customto yield an oil
  7. customChromatography 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

Quellen und Nachweise

ORD-Eintrag
ord-aaf5a42a752744d18f4fe815940c0b84
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04151199

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