Hydrochloric Acid → 3-(Trifluoromethyl)-1,2-oxazole-4-carboxylic acid

HRID 1094805Notes

Reaction equation

HRID 1094805 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:11]([F:14])([F:13])[F:12])=[N:8][O:9][CH:10]=1)=[O:5])C.Cl.O>C(O)(=O)C>[F:14][C:11]([F:12])([F:13])[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 57582321HCID 57582321, compound

Product 1

HCID 510638063-(Trifluoromethyl)-1,2-oxazole-4-carboxylic acidYield 8.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

3-Trifluoromethyl-isoxazole-4-carboxylic acid ethyl ester (Preparation 47, 1.00 g, 4.78 mmol), glacial acetic acid (4 ml), concentrated hydrochloric acid (2 ml, 20 mmol) and water (2 ml, 200 mmol) were heated together with stirring at 70° C. for 2 hours. Solvents were removed by evaporation in vacuo and the residue was left to stand at room temperature for 16 hours. Water (40 ml) and t-butylmethyl ether (80 ml) was added and the layers separated. The organic layer was washed with dilute hydrochloric acid (20 ml), then dried over anhydrous Na2SO4 (s), filtered and evaporated in vacuo to afford the title compound as a brown gum (70 mg, 8%). Material was taken on with no further purification.

Workup

  1. customSolvents were removed by evaporation in vacuo
  2. waitthe residue was left
  3. waitto stand at room temperature for 16 hours
  4. additionWater (40 ml) and t-butylmethyl ether (80 ml) was added
  5. customthe layers separated
  6. washThe organic layer was washed with dilute hydrochloric acid (20 ml)
  7. dry with materialdried over anhydrous Na2SO4 (s)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-89bba47ed6f04cf29bf9d990a4f45f8f
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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