4-bromo-1-methyl-1H-pyrazole-5-carbaldehyde → (4-bromo-1-methyl-1H-pyrazol-5-yl)methanol

HRID 1480890

Reaction equation

HRID 1480890 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH3:9])[C:6]=1[CH:7]=[O:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH3:9])[C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 27946344-bromo-1-methyl-1H-pyrazole-5-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 57415773(4-bromo-1-methyl-1H-pyrazol-5-yl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-1-methyl-1H-pyrazole-5-carbaldehyde (677 mg, 3.58 mmol) in MeOH (8 mL) at 0° C., NaBH4 (136 mg, 0.86 mmol) was added. The solution was stirred at room temperature for 2 hours. The reaction was concentrated in vacuo and diluted with water. The solution was extracted with EtOAc, the organic layer collected, dried over sodium sulphate and concentrated in vacuo to afford the title compound as a white solid (614 mg, 90%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with water
  3. extractionThe solution was extracted with EtOAc
  4. customthe organic layer collected
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8315fbc0f7541bc99a71670c81ff94d
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Linked notes

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