[2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-acetic acid → 2-[2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-ethanol

HRID 915420Notes

Reaction equation

HRID 915420 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][C:8](O)=[O:9])=[CH:5][C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:3]1>O1CCCC1>[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][OH:9])=[CH:5][C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)=[N:3]1

Participants

3

Reactant 1

HCID 69282814[2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-acetic acid

Product 1

HCID 692830492-[2-Methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of [2-methyl-5-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-acetic acid (286 mg, 1 mmol) in tetrahydrofuran (4 ml) was treated at 0° C. with a 1 M solution of BH3*THF in tetrahydrofuran (2.5 ml, 3 mmol). The cooling bath was removed and the reaction mixture stirred at ambient temperature for 16 h. Careful quenching with MeOH and ice water, twofold extraction with AcOEt, washing with ice water/brine 1/1, drying over magnesium sulfate, and evaporation of the solvent left a crude product which was refluxed for 30 min in MeOH to liberate quantitatively the free alcohol. The solvent was evaporated in vacuo to yield 273 mg (1 mmol, quant.) of the title compound as colorless crystals.

Workup

  1. customThe cooling bath was removed
  2. customCareful quenching with MeOH and ice water, twofold extraction with AcOEt
  3. washwashing with ice water/brine 1/1
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvent
  5. waitleft a crude product which
  6. temperaturewas refluxed for 30 min in MeOH
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-68acae5ed9ee4fccaa47b3ec5c9f6723
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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