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

HRID 523107

Reaction equation

HRID 523107 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-292f601f3fab4682ac53935aab33a93b
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Linked notes

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