Chloroform → Ethyl 5-phenyl-1,2-oxazole-4-carboxylate

HRID 1816615Notes

Reaction equation

HRID 1816615 reaction equation
[C:1]1(C#C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:10](=NO)[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:18](=[O:21])([O-])[O-].[K+].[K+].[Cl-].[NH4+:25].[CH:26](Cl)(Cl)Cl>O>[C:1]1([C:18]2[O:21][N:25]=[CH:26][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 6212ChloroformHCID 10821PhenylacetyleneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 6816376Ethyl chloro(hydroximino)acetate

Product 1

HCID 11481356Ethyl 5-phenyl-1,2-oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g of phenyl acetylene and 1.48 g of ethyl 2-chloro-2-hydroxyiminoacetate were dissolved in 20 ml chloroform, and 1.4 g of potassium carbonate was added thereto, and the mixture was stirred at room temperature for 16 hours. Water and aqueous ammonium chloride solution were added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1), to give 1.2 g of ethyl 5-phenyl-4-isoxazole carboxylate.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-49b7dfebc531440487f3d3862f596fd1
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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