Ethyl 5-phenyl-1,2-oxazole-4-carboxylate → 5-Phenylisoxazole-4-carboxylic acid

HRID 1389020Notes

Reaction equation

HRID 1389020 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5])C.C(OC(C1C=NOC=1C1C=CC(Cl)=CC=1Cl)=O)C>C1(C)C=CC=CC=1>[C:11]1([C:10]2[O:9][N:8]=[CH:7][C:6]=2[C:4]([OH:5])=[O:3])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 11481356Ethyl 5-phenyl-1,2-oxazole-4-carboxylateHCID 22221209HCID 22221209, compound

Product 1

HCID 147872535-Phenylisoxazole-4-carboxylic acidYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The procedure of Example 27 was employed utilizing ethyl-5-phenyl-4-isoxazolecarboxylate in lieu of ethyl-5-(2',4'-dichlorophenyl)-4-isoxazolecarboxylate to yield upon recrystallization with toluene, 5-phenyl-4-isoxazolecarboxylic acid (7.5 g.; 55% yield) as a white solid having a melting point of 153°-154° C. and the following analysis:

Sources & evidence

ORD record
ord-c13afc80eebd4a2c823485234fbcbcb1
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

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