Water → (5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-yl)-methanol

HRID 1292787Notes

Reaction equation

HRID 1292787 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:11]=[C:10]([C:19]([F:22])([F:21])[F:20])[C:9]=1[CH:23]=[O:24].C(OCC)(=O)C.O>C1COCC1>[Cl:7][C:8]1[N:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:11]=[C:10]([C:19]([F:21])([F:20])[F:22])[C:9]=1[CH2:23][OH:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14790525-chloro-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 17862912(5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-yl)-methanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

A solution of 0.21 g (5.5 mmoles) of lithium aluminum hydride dissolved in 70 ml of THF was cooled to -30° C. Thereto was gradually added a solution of 3 g (10.9 mmoles) of 5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazole-4carboaldehyde dissolved in 30 ml of tetrahydrofuran. The resulting mixture was stirred at −30° C. for 30 minutes to give rise to a reaction. After the completion of the reaction, ethyl acetate was added, followed by stirring. Then, water was added, followed by stirring for a while. The reaction mixture was filtered under vacuum. The filtrate was extracted 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 3.0 g (yield: 99.9%) of (5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazol-4-yl)-methanol as white crystals.

Workup

  1. customto give rise
  2. customto a reaction
  3. additionwas added
  4. stirringby stirring
  5. stirringby stirring for a while
  6. filtrationThe reaction mixture was filtered under vacuum
  7. extractionThe filtrate was extracted with ethyl acetate
  8. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe resulting solution was subjected to vacuum distillation
  11. customto remove the solvent

Sources & evidence

ORD record
ord-f1fdcb4890e740d6a96071ffc74dd11b
Source dataset
uspto-grants-2007_07
Patent number
US07238689B2

Reaction notes

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