Diethyl Ether → Ethyl 5-phenyl-1,2-oxazole-4-carboxylate

HRID 1389006Notes

Reaction equation

HRID 1389006 reaction equation
Cl.NO.[CH2:4]([O:6][C:7](=[O:21])[C:8]([C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:9][N:10](C)C)[CH3:5].C([O-])(=O)C.[Na+].CCOCC>CO>[CH2:4]([O:6][C:7]([C:8]1[CH:9]=[N:10][O:20][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:21])[CH3:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54499154Ethyl-2-benzoyl-3-dimethylaminopropenoate

Product 1

HCID 11481356Ethyl 5-phenyl-1,2-oxazole-4-carboxylateYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (1.1 g.; 0.016 mol.) was added to a mixture of ethyl-2-benzoyl-3-dimethylaminopropenoate (3.71 g.; 0.015 mol.) and anhydrous sodium acetate (1.25 g.; 0.015 mol.) in 50 ml. of ether and 25 ml. of methanol at 25° C. After 16 hours, the solvent was removed by evaporation and the residue was extracted with five 50 ml. portions of ether. The ether extracts were combined, washed with water, dried, filtered, then concentrated to yield an oil which was further purified by evaporative distillation at 60° C. and 0.55 torr. to yield ethyl-5-phenyl-4-isoxazolecarboxylate (1.03 g.; 32% yield) as a colorless liquid having the following analysis:

Workup

  1. customat 25° C
  2. customthe solvent was removed by evaporation
  3. extractionthe residue was extracted with five 50 ml
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield an oil which
  9. distillationwas further purified by evaporative distillation at 60° C.

Sources & evidence

ORD record
ord-96f8ebd1c70149069d95d1ba00c35386
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

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