Sodium borohydride → [5-Chloro-3-(4-chloro-phenyl)-1-phenyl-1H-pyrazol-4-yl]-methanol

HRID 441861Notes

Reaction equation

HRID 441861 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:7]=[C:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:5]=1[CH:22]=[O:23]>CN(C)C=O.O>[Cl:3][C:4]1[N:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:7]=[C:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:5]=1[CH2:22][OH:23]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 214183605-Chloro-3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 53664379[5-Chloro-3-(4-chloro-phenyl)-1-phenyl-1H-pyrazol-4-yl]-methanolYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.8 g of sodium borohydride are added to a suspension of 46.4 g of 5-chloro-3-p-chlorophenyl-1-phenyl-pyrazole-4-carboxaldehyde in 700 ml of dimethylformamide and 100 ml of water, the temperature possibly rising to 35°. After 30 minutes purification is carried out with active charcoal, precipitation is carried out with 700 ml of water and the precipitate is well washed. 5-Chloro-3-p-chlorophenyl-4-hydroxymethyl-1-phenyl-pyrazole is obtained with a 95 % yield; F 152.5°-153.5° (from acetone).

Workup

  1. custompossibly rising to 35°
  2. customAfter 30 minutes purification
  3. customis carried out with active charcoal, precipitation
  4. washthe precipitate is well washed

Sources & evidence

ORD record
ord-0e97d15a43414714a82dcfb62f4642b4
Source dataset
uspto-grants-1977_08
Patent number
US04042702

Reaction notes

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