Water → (5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl)methanol

HRID 1292809Notes

Reaction equation

HRID 1292809 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:10])[F:9])[C:3]=1[CH:11]=[O:12].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([F:9])[F:10])[C:3]=1[CH2:11][OH:12]

Participants

5

Conditions

Temperature
0 °C

Procedure

A solution of 7.2 g (37.0 mmoles) of 5-chloro-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboaldehyde dissolved in 100 ml of methanol was cooled to 0° C. Thereto was gradually added 2.1 g (55.5 mmoles) of sodium borohydride. The mixture was stirred at room temperature for 3 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 3.8 g (yield: 52.1%) of (5-chloro-3-difluoromethyl-1-methyl-1H-pyrazol-4-yl)-methanol.

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter the completion of the reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent

Sources & evidence

ORD record
ord-d6c664937e5a44c08ddea4cb267a9a43
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

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