Hydrochloric Acid → 3-(4-Hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)propanoic acid

HRID 1381372Notes

Reaction equation

HRID 1381372 reaction equation
C(OC([O:6][C:7]1[C:11](=[O:12])[O:10][CH:9]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:8]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[OH:6][C:7]1[C:11](=[O:12])[O:10][CH:9]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:8]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 13389582HCID 13389582, compound

Product 1

HCID 1283563-(4-Hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)propanoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-Ethoxycarbonyloxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionic acid (20 mg) was dissolved in methanol (3 ml), and 10% aqueous potassium carbonate (3 ml) was added. The mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water (10 ml), acidified with hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was then distilled off. The remaining oil was purified by preparative silice gel thin layer chromatography (developer: 5% methanol-chloroform). Recrystallization from chloroform gave 3-(4-hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionic acid (11 mg) as colorless needles. m.p. 177°-179° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. customThe remaining oil was purified by preparative silice gel thin layer chromatography (developer: 5% methanol-chloroform)
  6. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-8c10bd39fd584beba709a74aea824a17
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Reaction notes

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