Lithium hydroxide, monohydrate → 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid

HRID 1471658Notes

Reaction equation

HRID 1471658 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]([O:12]C)=[O:11])[N:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)[CH:2]=[CH2:3].O.[OH-].[Li+]>C1COCC1.O.CO>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]([OH:12])=[O:11])[N:7]=[C:6]([C:14]([F:16])([F:17])[F:15])[CH:5]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 90281162methyl 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 902814622-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acidYield 99%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate (120 mg, 0.48 mmol) was dissolved in THF (1 mL). To this solution was added lithium hydroxide monohydrate (70 mg) in water (1 mL) and MeOH (0.1 mL). The resulting solution was stirred at room temperature overnight. Upon completion of the reaction, the product was purified by reverse phase HPLC eluting with acetonitrile/water (with 0.1% TFA) to afford 2-(5-allyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid (110 mg, 99%) as an oil. MS (m/z): 235.3 [M+H]+; HPLC retention time 3.03 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Workup

  1. customUpon completion of the reaction
  2. customthe product was purified by reverse phase HPLC
  3. washeluting with acetonitrile/water (with 0.1% TFA)

Sources & evidence

ORD record
ord-d0213fa3bafd4ca196dfe611fb4bf4c4
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

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