Sodium Acetate → 3-{2-Methyl-4-[2-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl}propanoic acid

HRID 1982443Notes

Reaction equation

HRID 1982443 reaction equation
Cl[CH:2]([CH2:6][C:7]1[O:11][C:10]([CH3:12])=[N:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20])[C:3]([OH:5])=[O:4].C([O-])(=O)C.[Na+]>C(O)C>[CH3:12][C:10]1[O:11][C:7]([CH2:6][CH2:2][C:3]([OH:5])=[O:4])=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:20])([F:21])[F:22])[N:9]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 13646805HCID 13646805, compound

Product 1

HCID 136468023-{2-Methyl-4-[2-(trifluoromethyl)phenyl]-1,3-oxazol-5-yl}propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-3-[2-methyl-4-(2-trifluoromethylphenyl)-5-oxazolyl]propionic acid (2.5 g), sodium acetate (0.62 g), 80% ethanol (50 ml) and 10% paladium-carbon (1.0 g) was subjected to catalytic hydrogenation for 8 hours and then the catalyst was filtered off. The filtrate was concentrated, diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and iso-propyl ether was added to the residue to give crystals of 2-methyl-4-(2-trifluoromethylphenyl)oxazole-5-propionic acid, yield 1.85 g (82.6%). Recrystallization from ether gave colorless prisms. yield 1.45 g (64.7%), m.p. 118°-119° C.

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. additioniso-propyl ether was added to the residue

Sources & evidence

ORD record
ord-6986c1d48ab1409386242ab355b1595d
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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