Sodium Hydroxide → HCID 22714140, compound

HRID 434059Notes

Reaction equation

HRID 434059 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[C:16]([I:18])[CH:15]=[CH:14][C:13]=2[F:19])=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+]>CCO>[C:4]([C:6]1[C:7]([C:12]2[CH:17]=[C:16]([I:18])[CH:15]=[CH:14][C:13]=2[F:19])=[N:8][O:9][C:10]=1[CH3:11])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18756276HCID 18756276, compound

Product 1

HCID 22714140HCID 22714140, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-ethoxycarbonyl-5-methyl-3-(2-fluoro-5-iodophenyl)isoxazole (1.04 g, 2.77 mmol) in EtOH (14 ml) was added 5N NaOH (1.11 ml, 5.6 mmol, 2 eq.) and stirred in a 50° C. oil bath for 1 hr. Rxn was cooled to room temperature, poured into ice H2O and extracted with Et2O. Acidified aqueous layer to pH 2 using conc. HCl and extracted with ethyl acetate. The combined organic solution was washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound (0.85 g, 86%).

Workup

  1. temperatureRxn was cooled to room temperature
  2. extractionextracted with Et2O
  3. extractionextracted with ethyl acetate
  4. washThe combined organic solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-03b6fdca88e04f8097190770a63f0131
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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