Sodium Hydroxide → [5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetic acid

HRID 479132Notes

Reaction equation

HRID 479132 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][C:18]#N.[OH-:20].[Na+].CCO.[OH2:25]>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][C:18]([OH:25])=[O:20]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 18003422[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetonitrileHCID 19096565Water ethanol

Product 1

HCID 18003528[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetic acid

Procedure

8.69 g of the above prepared [5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetonitrile (32.6 mmol) was dissolved in 100 ml EtOH/water=1/1 and treated with 10 eq. of NaOH-pellets (13 g). Hydrolysis was allowed to proceed over night at 85° C. Pouring onto crashed ice/HCl, twofold extraction with AcOEt, washing with water, drying over magnesium sulfate, evaporation of the solvents, followed by recrystallization from AcOEt/hexane, yielded 7.35 g of the title acid as off-white crystals.

Workup

  1. customHydrolysis
  2. waitto proceed over night at 85° C
  3. additionPouring
  4. extractionice/HCl, twofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over magnesium sulfate, evaporation of the solvents
  7. customfollowed by recrystallization from AcOEt/hexane

Sources & evidence

ORD record
ord-b8b238977a724423ba3f40ae1b2fcde4
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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