Lithium Hydroxide → HCID 21071151, compound

HRID 1372137Notes

Reaction equation

HRID 1372137 reaction equation
C[O:2][C:3](=[O:24])[CH:4]([N:13]1[C:17]([CH3:18])=[C:16]([Cl:19])[C:15]([C:20]([F:23])([F:22])[F:21])=[N:14]1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1.[Li+].[OH-]>C1COCC1.O>[Cl:19][C:16]1[C:15]([C:20]([F:22])([F:21])[F:23])=[N:14][N:13]([CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=2)[C:3]([OH:24])=[O:2])[C:17]=1[CH3:18]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58778063HCID 58778063, compound

Product 1

HCID 21071151HCID 21071151, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-(3-methoxy-phenyl)-acetic acid methyl ester was then dissolved in THF (20 ml) and LiOH (0.39 g) in water (5 ml) were added. The mixture was stirred at room temperature for 4 h. After this period the THF was completely evaporated from the reaction mixture under vacuum. The remaining aqueous layer was extracted with ethyl acetate (3×5 ml) and the organic layer was discarded. The aqueous layer was cooled in ice and neutralized by using concentrated HCl. This neutral aqueous layer was extracted with ethyl acetate (3×10 ml), the organic layer dried over Na2SO4, concentrated and purified by flash chromatography (CHCl3/MeOH) to yield (4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-(3-methoxy-phenyl)-acetic acid

Workup

  1. customAfter this period the THF was completely evaporated from the reaction mixture under vacuum
  2. extractionThe remaining aqueous layer was extracted with ethyl acetate (3×5 ml)
  3. temperatureThe aqueous layer was cooled in ice
  4. extractionThis neutral aqueous layer was extracted with ethyl acetate (3×10 ml)
  5. dry with materialthe organic layer dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-9f3c2063cc5246ad9b9c7195a1c6f1b6
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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