Oxalic Acid → HCID 73791796, compound

Participants

Reaction Steps

Methyl 3-[3-hydroxy-5-oxo-2-(3-oxodec-1-enyl)cyclopent-1-enyl]propanoate (2.1g.) was dissolved in EtOH/H2O 9:1 (30ml.) and chilled in an ice bath. Triethylamine (0.95ml.) was added followed by sodium borohydride (0.24g.) dissolved in water (2ml.). The reaction mixture was stirred for fifteen minutes and then water was added, followed by dilute oxalic acid solution to adjust the pH to 5. Ethyl acetate extraction, washing and drying of the extract followed by evaporation gave an oil. This was chromatographed on silicic acid, using as an eluent: MeOH/CHCl3. The appropriate fractions containing the major component were combined and evaporated to dryness (~800mg.oil). This was rechromatographed using a similar column. In this way, pure Methyl 3-[3-hydroxy-5-oxo-2-(3-hydroxydec-1-enyl)cyclopent-1-enyl]propanoate was obtained. Spectroscopic data was in full accord with the expected structure of the final product.

Provenance & Evidence