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

HRID 26669Notes

Reaction equation

HRID 26669 reaction equation
[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]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 70603560HCID 70603560, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aaf5a42a752744d18f4fe815940c0b84
Source dataset
uspto-grants-1979_04
Patent number
US04151199

Reaction notes

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