Water → 5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-methanol
Reaction equation
[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH:12]=[O:13].[BH4-].[Na+].O.C(OCC)(=O)C>CO>[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:10])([F:9])[F:11])[C:3]=1[CH2:12][OH:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 36.8 g (187.6 mmoles) of 5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde dissolved in 200 ml of methanol was added, with ice-cooling, into a solution of 3.9 g (102.6 mmoles) of sodium borohydride dissolved in 500 ml of methanol. The mixture was stirred at 0° C. for 30 minutes to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water and extraction with ethyl acetate was conducted. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein, to obtain 35.4 g (yield: 95.4%) of (5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-methanol.
Workup
- additionwas added, with ice-
- customto give rise
- customto a reaction
- customAfter confirmation of the completion of the reaction
- washThe resulting organic layer was washed with water
- dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
- distillationThe resulting solution was subjected to reduced pressure distillation
- customto remove the solvent
Sources & evidence
- ORD record
- ord-e7fb13350fbb47c9be9b300eae8860b7
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07875606B2
Reaction notes
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