5-Chloro-1,3-dimethylpyrazole-4-carboxaldehyde → (5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methanol

HRID 577050Notes

Reaction equation

HRID 577050 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([CH3:10])[C:5]=1[CH:11]=[O:12]>CO>[Cl:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([CH3:10])[C:5]=1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 13673186(5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium borohydride (358 mg, 9.5 mmol) in methanol (15 mL) was added a solution of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (1.0 g, 6.3 mmol) in methanol (5 mL) at 0° C. The mixture was stirred overnight at room temperature. The solvent was evaporated, water was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, (5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methanol was obtained as a white solid (690 mg, 68% yield) and used in the next step without further purification; 1H NMR (400 MHz, CDCl3): δ 1.53 (t, J=5.5 Hz, 1H), 2.28 (s, 3H), 3.77 (s, 3H), 4.49 (d, J=5.5 Hz, 2H).

Workup

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

Sources & evidence

ORD record
ord-85eb492c2ad04803a3f94dff1e9d97ae
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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