Acetic Acid → 4-Ethyl-5-phenylisoxazole-3-carboxylic acid

HRID 1804460Notes

Reaction equation

HRID 1804460 reaction equation
[CH2:1]([C:3]1[C:4]([C:14]([O:16]C)=[O:15])=[N:5][O:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[OH-].[Na+].C(O)(=O)C>CO>[CH2:1]([C:3]1[C:4]([C:14]([OH:16])=[O:15])=[N:5][O:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 58537177Methyl 4-ethyl-5-phenylisoxazole-3-carboxylate

Product 1

HCID 548465634-Ethyl-5-phenylisoxazole-3-carboxylic acidYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-ethyl-5-phenylisoxazole-3-carboxylate (194 mg, 0.839 mmol) and 1N aqueous sodium hydroxide (1.26 mL, 1.258 mmol) in methanol (3 mL) was heated to 100° C. for 10 minutes under microwave. The reaction mixture was acidified with acetic acid until the pH was about 4. The mixture was concentrated, and the residue was suspended in water (2 mL) and stirred for 20 minutes. The solid was collected by vacuum filtration and dried to give 4-ethyl-5-phenylisoxazole-3-carboxylic acid (148 mg). The compound had an HPLC ret. time=2.93 min.−Column: YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO; Solvent B=90% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100. LC-MS: M+1=218+.

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationThe solid was collected by vacuum filtration
  3. customdried

Sources & evidence

ORD record
ord-b2dfd47a4ca14a44a07f0bbe0adbc7c4
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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