Lithium hydroxide, monohydrate → HCID 59632339, compound

HRID 2369073Notes

Reaction equation

HRID 2369073 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[C:15]([CH:22]=[CH:23][CH:24]=2)[O:16][CH2:17][C:18]([O:20]C)=[O:19])=[CH:11][C:10]([C:25]([F:28])([F:27])[F:26])=[N:9]1.O.[OH-].[Li+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[C:15]([CH:22]=[CH:23][CH:24]=2)[O:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][C:10]([C:25]([F:28])([F:26])[F:27])=[N:9]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59631873HCID 59631873, compound

Product 1

HCID 59632339HCID 59632339, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(3-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenoxy)acetate (140 mg, 0.34 mmol) in MeOH (5 mL), was added lithium hydroxide monohydrate (60 mg, 1.42 mmol). The resulting mixture was stirred at ambient temperature for 18 hours. The reaction mixture was then concentrated under reduced pressure and the residue was taken up in CH2Cl2 and H2O. The aqueous was made acidic by the addition of 1 N HCl. The layers were separated and the acidic aqueous was further extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. This white solid was taken up in warm CH2Cl2 and hexane and the resulting solution was cooled in an ice bath. Filtration, washing with hexane and drying of the precipitated solids afforded 2-(3-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenoxy)acetic acid (69 mg, 51% yield) as a white solid. MS(ES): 397 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionThe aqueous was made acidic by the addition of 1 N HCl
  3. customThe layers were separated
  4. extractionthe acidic aqueous was further extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. temperaturehexane and the resulting solution was cooled in an ice bath
  9. filtrationFiltration
  10. washwashing with hexane
  11. customdrying of the precipitated solids

Sources & evidence

ORD record
ord-d082e5e9c87b4d54917f92c821b6d5f7
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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