1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid → (1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol

HRID 2036133Notes

Reaction equation

HRID 2036133 reaction equation
[CH3:1][N:2]1[C:6]([C:7](O)=[O:8])=[CH:5][C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[CH:5][C:4]([C:10]([F:11])([F:12])[F:13])=[N:3]1

Participants

4

Reactant 2

HCID 6065401-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 58456726(1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid BB4a (837 mg, 4.3 mmol) is dissolved in anhydrous tetrahydrofurane (10 mL), then LiAlH4 (2.16 mL of 2.0 M in tetrahydrofurane, 4.3 mmol) is added dropwise and stirred at rt for 1 h. The mixture is quenched by dropwise addition of 1N HCl, then is made basic by addition of saturated NaHCO3 and extracted with EtOAc (3×). The organic layers are combined, washed with brine, dried (MgSO4), filtered and concentrated to provide (1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanol BB4b as a clear oil. 1H NMR (400 MHz, CDCl3) δ=6.46 (s, 1H), 4.69 (d, J=5.6 Hz, 2H), 3.95 (s, 3H); MS calcd. for C6H8F3N2O ([M+H]+): 181.0, found: 181.1.

Workup

  1. customThe mixture is quenched by dropwise addition of 1N HCl
  2. additionis made basic by addition of saturated NaHCO3
  3. extractionextracted with EtOAc (3×)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-85791cebbacb4345b86431e476d4ccee
Source dataset
uspto-grants-2013_11
Patent number
US08575168B2

Reaction notes

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