Water → HCID 13920708, compound

HRID 2291633Notes

Reaction equation

HRID 2291633 reaction equation
[CH2:1]([O:3][C:4]1[C:8](=[O:9])[O:7][CH:6]([CH2:10][CH2:11][C:12]([O:14]C)=[O:13])[C:5]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2].[OH-].[Na+].O>CO>[CH2:1]([O:3][C:4]1[C:8](=[O:9])[O:7][CH:6]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:5]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21279133HCID 21279133, compound

Product 1

HCID 13920708HCID 13920708, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(4-ethoxy-5-oxo-3-phenyl2,5-dihydro-2-furyl)propionate (0.20 g) in methanol (2 ml) was added 1N sodium hydroxide solution (0.8 ml) during a period of a few minutes at ambient temperature. The solution was stirred for 30 minutes at the same temperature and then poured into water (10 ml). The mixture was washed with diethyl ether and the aqueous layer was adjusted to pH 1 with aqueous 10% hydrochloric acid. The separated oil was extracted with ethyl acetate twice. The combined organic layers were washed with water three times, dried, and evaporated to dryness. The residue was crystallized from a mixture of diethyl ether and n-hexane to yield 3-(4-ethoxy-5-oxo-3-phenyl2,5-dihydro-2-furyl)propionic acid (121 mg) as a crystal.

Workup

  1. washThe mixture was washed with diethyl ether
  2. extractionThe separated oil was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with water three times
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was crystallized from a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-5e6c0d42e6474ba78801577b102c0da8
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

Loading…