Lithium hydroxide, monohydrate → HCID 57507619, compound

HRID 1930328Notes

Reaction equation

HRID 1930328 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([O:12]CC)=[O:11])[N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.CCO.O.O[Li].O>Cl>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 18504229Ethanol tetrahydrofuran waterHCID 69042455Ethyl 3-(1,1-dimethylethyl)-1-(3-fluorophenyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 57507619HCID 57507619, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirring solution of ethyl 3-tert-butyl-1-(3-fluorophenyl)-1H-pyrazole-5-carboxylate (0.786 g, 2.71 mmol) in 1:1:1 THF/EtOH/H2O (36 ml) at RT was added LiOH.H2O (0.568 g, 13.5 mmol). After stirring at RT overnight, the reaction mixture was diluted with 3M HCl (30 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (2×30 mL), dried (MgSO4) and concentrated to afford 3-tert-butyl-1-(3-fluorophenyl)-1H-pyrazole-5-carboxylic acid (0.602 g, 85% yield) as white solid. MS (ESI) m/z: 263 (M+H+).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with brine (2×30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0084d91da2ff4d96adcc2c7f2fee8351
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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