Sodium Hydroxide → 5-Methyl-3-(trifluoromethyl)-1,2-oxazole-4-carboxylic acid

HRID 2186453Notes

Reaction equation

HRID 2186453 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]([F:15])([F:14])[F:13])=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+]>O1CCCC1.O>[CH3:11][C:10]1[O:9][N:8]=[C:7]([C:12]([F:15])([F:13])[F:14])[C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136639574-Ethoxycarbonyl-5-methyl-3-trifluoromethylisoxazole

Product 1

HCID 224566395-Methyl-3-(trifluoromethyl)-1,2-oxazole-4-carboxylic acidYield 80.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 5-methyl-3-trifluoromethylisoxazole-4-carboxylic acid ethyl ester (2.0 g) and sodium hydroxide (1.1 g) in tetrahydrofuran/water (20 ml/20 ml) was heated at reflux for 18 hours. The tetrahydrofuran was removed in vacuo and the aqueous residue washed with ethyl acetate (50 ml), acidified to pH2 with conc. hydrochloric acid and extracted with ethyl acetate (100 ml). The organic layer was washed with brine (50 ml), separated, dried over magnesium sulphate, filtered and concentrated in vacuo to afford the title compound as a peach-coloured solid (1.4 g).

Workup

  1. temperatureat reflux for 18 hours
  2. customThe tetrahydrofuran was removed in vacuo
  3. washthe aqueous residue washed with ethyl acetate (50 ml)
  4. extractionextracted with ethyl acetate (100 ml)
  5. washThe organic layer was washed with brine (50 ml)
  6. customseparated
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eda67af6e2be4901a55c0f2b6cd3a7f4
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

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