4-chloro-1-methyl-1H-pyrazole-3-carbaldehyde → (4-chloro-1-methyl-1H-pyrazol-3-yl)methanol

HRID 577141Notes

Reaction equation

HRID 577141 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([CH:10]=[O:11])=[N:6][N:7]([CH3:9])[CH:8]=1>CO>[Cl:3][C:4]1[C:5]([CH2:10][OH:11])=[N:6][N:7]([CH3:9])[CH:8]=1

Participants

4

Reactant 2

HCID 27821534-chloro-1-methyl-1H-pyrazole-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 55255171(4-chloro-1-methyl-1H-pyrazol-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium borohydride (393 mg, 10.4 mmol) in methanol (25 mL) was added a solution of 4-chloro-1-methyl-1H-pyrazole-3-carbaldehyde (1.0 g, 6.9 mmol) in methanol (10 mL) at 0° C. The mixture was stirred for 4 hours at room temperature. The solvent was evaporated, water was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic phases were washed with brine and dried over sodium sulfate. After evaporation of the solvent, (4-chloro-1-methyl-1H-pyrazol-3-yl)methanol was obtained as a yellow oil (680 mg, 67% yield) and used in the next step without further purification; 1H NMR (400 MHz, DMSO-d6): δ 3.77 (s, 3H), 4.34 (d, J=5.6 Hz, 2H), 5.03 (s, J=5.6 Hz, 1H), 7.85 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-a5b7acb1356a452994d9cb13593fc378
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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