Trifluoroacetic acid → 5-Chloro-3-(4-methoxy-3-methylphenyl)-1,4-dimethyl-1H-pyrazole

HRID 628534Notes

Reaction equation

HRID 628534 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([CH3:16])[CH:9]=2)[C:3]=1[CH:17]=O.FC(F)(F)C(O)=O.C[SiH](C)C>O>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([CH3:16])[CH:9]=2)[C:3]=1[CH3:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 70435TrimethylsilaneHCID 1180012805-Chloro-3-(4-methoxy-3-methylphenyl)-1-methyl-1H-pyrazole-4-carboxaldehyde

Product 1

HCID 1180013285-Chloro-3-(4-methoxy-3-methylphenyl)-1,4-dimethyl-1H-pyrazoleYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At 0° C., a mixture of 5-chloro-4-formyl-3-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole (described in Reference Preparation example 91) 0.3 g and trifluoroacetic acid 10 ml was added trimethylsilane 0.27 g. The resulting mixture was stirred at room temperature for three hours, and thereto was added water 5 ml. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 5-chloro-3-(4-methoxy-3-methyl-phenyl)-1,4-dimethyl-1H-pyrazole 0.28 g.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-89ee07d7c92b40e98ba3bad38672f47c
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

Loading…