Sodium borohydride → [1-methyl-5-(oxetan-3-yloxy)-3-trifluoromethyl-1H-pyrazol-4-yl]-methanol

HRID 1192945Notes

Reaction equation

HRID 1192945 reaction equation
[CH3:1][N:2]1[C:6]([O:7][CH:8]2[CH2:11][O:10][CH2:9]2)=[C:5]([CH:12]=[O:13])[C:4]([C:14]([F:17])([F:16])[F:15])=[N:3]1.[BH4-].[Na+]>CO>[CH3:1][N:2]1[C:6]([O:7][CH:8]2[CH2:11][O:10][CH2:9]2)=[C:5]([CH2:12][OH:13])[C:4]([C:14]([F:17])([F:15])[F:16])=[N:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 597395451-methyl-5-(oxetan-3-yloxy)-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 59739609[1-methyl-5-(oxetan-3-yloxy)-3-trifluoromethyl-1H-pyrazol-4-yl]-methanolYield 69.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-Methyl-5-(oxetan-3-yloxy)-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde (11.6 g, 46.4 mmol) was dissolved in methanol (100 ml) and sodium borohydride (0.87 g, 23.0 mmol) was added in portions at 0° C. After stirring at 0° C. for 2 hours the mixture was concentrated and the oil was dissolved in dichloromethane (100 ml). The solution was washed with water and brine, dried over magnesium sulfate and concentrated to give the product as yellow solid (8.14 g) which was used in the next step without further purification.

Workup

  1. concentrationwas concentrated
  2. dissolutionthe oil was dissolved in dichloromethane (100 ml)
  3. washThe solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a1fe51267594677b49c82afc34b9f86
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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