Water → HCID 22934882, compound

HRID 254224Notes

Reaction equation

HRID 254224 reaction equation
[CH2:1]([N:3]1[C:7]([F:8])=[C:6]([CH:9]=[O:10])[C:5]([C:11]([F:14])([F:13])[F:12])=[N:4]1)[CH3:2].[BH4-].[Na+].O.C(OCC)C>CO>[CH2:1]([N:3]1[C:7]([F:8])=[C:6]([CH2:9][OH:10])[C:5]([C:11]([F:13])([F:12])[F:14])=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 22934875HCID 22934875, compound

Product 1

HCID 22934882HCID 22934882, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 11.1 g (52.8 mmoles) of 1-ethyl-5-fluoro-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde dissolved in 50 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 and extraction with diethyl ether was conducted. 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 reduced pressure distillation to remove the solvent contained therein, to obtain 9.1 g (yield: 81.3%) of (1-ethyl-5-fluoro-3-trifluoromethyl-1H-pyrazol-4-yl)-methanol.

Workup

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

Sources & evidence

ORD record
ord-84c73a59f7fd4d518317af779525799f
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Reaction notes

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