Lithium Hydroxide → HCID 178524630, compound

HRID 1970585Notes

Reaction equation

HRID 1970585 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([OH:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:7]=1)=[O:5])C.[Li+].[OH-].[OH-].[Na+]>C1COCC1.O>[OH:11][C:9]1[N:8]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 178469353HCID 178469353, compound

Product 1

HCID 178524630HCID 178524630, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.00 g 5-Hydroxy-1-(4-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester in 20 ml THF and 6 ml water were added 480 mg LiOH. After 12 h additional 2 ml 2 N NaOH were added to complete ester hydrolysis. The organic solvent was removed in vacuo, the aqueous phase extracted once with ethyl acetate and the aqueous phase acidified with 6 M HCl. The suspension obtained was filtered and the filtrate saturated with NaCl before being extracted with ethyl acetate. The residue obtained after evaporation of the solvent was combined with the crude product after filtration and was found to be pure enough for the subsequent transformation.

Workup

  1. customThe organic solvent was removed in vacuo
  2. extractionthe aqueous phase extracted once with ethyl acetate
  3. customThe suspension obtained
  4. filtrationwas filtered
  5. extractionthe filtrate saturated with NaCl before being extracted with ethyl acetate
  6. customThe residue obtained
  7. customafter evaporation of the solvent
  8. filtrationafter filtration

Sources & evidence

ORD record
ord-e19f734abbe1402fb86c0fe45b5ff693
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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