Hydrochloric Acid → HCID 22713986, compound

HRID 434046Notes

Reaction equation

HRID 434046 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].CO.Cl>C1COCC1>[C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[N:8][O:9][C:10]=1[CH3:11])([OH:5])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 18756262Ethyl 3-(2,4-difluorophenyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 22713986HCID 22713986, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Ethoxycarbonyl-5-methyl-3-(2,4-difluorophenyl)isoxazole (305 mg, 1.14 mmol), 5N NaOH (1.0 ml, 5 mmol), methanol (5 ml), and THF (1 ml) were heated at 50° C. for 16 h. Ice was added and the pH was adjusted to 2-3 with 1N HCl. Extraction with EtOAc followed by washing (brine), drying (Na2SO4), filtering, and concentration gave the crude 4-carboxy-5-methyl-3-(2,4-difluorophenyl)isoxazole (286 mg, 99%) which was used without further purification.

Workup

  1. additionIce was added
  2. extractionExtraction with EtOAc
  3. washby washing (brine)
  4. dry with materialdrying (Na2SO4)
  5. filtrationfiltering
  6. concentrationconcentration

Sources & evidence

ORD record
ord-ca62a8dcc60e49e8b2323614dcf66cd0
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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