Hydrochloric Acid → 2-{2-[4-(Trifluoromethyl)phenyl]ethenyl}-1,3-oxazole-4-carboxylic acid

HRID 1271415Notes

Reaction equation

HRID 1271415 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[O:9][CH:10]=1)=[O:5])C.[OH-].[Na+].O.Cl>C1COCC1>[F:22][C:19]([F:20])([F:21])[C:16]1[CH:15]=[CH:14][C:13]([CH:12]=[CH:11][C:8]2[O:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69489493HCID 69489493, compound

Product 1

HCID 694874342-{2-[4-(Trifluoromethyl)phenyl]ethenyl}-1,3-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid ethyl ester (1.64 g, 5.2 mmol) is dissolved in THF (20 ml), treated with aq. NaOH (1N, 10.5 ml, 10.5 mmol) and stirred for 1 h at reflux temperature. After cooling water is added and the mixture acidified with aq. HCl (3N). The mixture is extracted with ethyl acetate (3×50 ml), the extract washed with brine (50 ml), dried over sodium sulfate and concentrated in vacuo yielding 2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid as a colorless solid. Yield 1.36 g (92%)

Workup

  1. temperatureat reflux temperature
  2. additionis added
  3. extractionThe mixture is extracted with ethyl acetate (3×50 ml)
  4. washthe extract washed with brine (50 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6abbfde869f74e6792220c13a13e3c4d
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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