Hydrochloric Acid → Ethyl 3-(4-methoxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)propanoate

HRID 2291628Notes

Reaction equation

HRID 2291628 reaction equation
[OH:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI.Cl>CN(C)C=O>[CH3:21][O:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13832246HCID 13832246, compound

Product 1

HCID 128354Ethyl 3-(4-methoxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 3-(4-hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionate (86 g) and potassium carbonate (51.62 g) in N,N-dimethylformamide (855 ml) was added dropwise methyl iodide (23.25 ml) at ambient temperature with stirring and the mixture was stirred for 2.5 hours at the same temperature. The solvent was evaporated in vacuo to give a residue which was poured into diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and brine successively and dried. Evaporation of the solvent gave ethyl 3-(4-methoxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionate which was recrystallized from diisopropyl ether (73.07 g).

Workup

  1. stirringthe mixture was stirred for 2.5 hours at the same temperature
  2. customThe solvent was evaporated in vacuo
  3. customto give a residue which
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and brine successively
  6. customdried
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-89951bb1a9a640c88d883b96d1989c7a
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

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