Oxalic Acid → HCID 73791796, compound

HRID 441331Notes

Reaction equation

HRID 441331 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:3]1[CH:14]=[CH:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C.[BH4-].[Na+].C(O)(=O)C(O)=O>CCO.O.O>[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:3]1[CH:14]=[CH:15][CH:16]([OH:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 73791792HCID 73791792, compound

Product 1

HCID 73791796HCID 73791796, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 19096565Water ethanolSolvent

Procedure

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.

Workup

  1. temperaturechilled in an ice bath
  2. extractionEthyl acetate extraction
  3. washwashing
  4. customdrying of the extract
  5. customfollowed by evaporation
  6. customgave an oil
  7. customThis was chromatographed on silicic acid
  8. additionThe appropriate fractions containing the major component
  9. customevaporated to dryness (~800mg.oil)
  10. customThis was rechromatographed

Sources & evidence

ORD record
ord-3fa7a68fd55f46918b14e721e7fe70f2
Source dataset
uspto-grants-1977_08
Patent number
US04039571

Reaction notes

Loading…