Hydrochloric Acid → HCID 57749173, compound

HRID 1874384Notes

Reaction equation

HRID 1874384 reaction equation
[CH2:1]([C:3]1[O:4][C:5]([C:13]([F:16])([F:15])[F:14])=[C:6]([C:8]([O:10]CC)=[O:9])[N:7]=1)[CH3:2].[OH-].[Na+].Cl>C(O)C>[CH2:1]([C:3]1[O:4][C:5]([C:13]([F:16])([F:15])[F:14])=[C:6]([C:8]([OH:10])=[O:9])[N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57749143HCID 57749143, compound

Product 1

HCID 57749173HCID 57749173, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2-ethyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylate (2.00 g, 8.43 mmol) in ethanol (10 mL) was added 8N aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at 50° C. for 1.5 hr. The reaction mixture was adjusted to pH 4 with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (800 mg, 45%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. filtrationthe residue was collected by filtration
  7. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-bdc057ea71584109a82bc4c1563e5234
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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