Methanol → 4-(Benzyloxy)-3,5-diphenyl-1H-pyrazole

HRID 1576252Notes

Reaction equation

HRID 1576252 reaction equation
[C:1]1([C:7]2[C:11]([OH:12])=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].CO.[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([O:12][C:11]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][NH:9][C:10]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7503Benzyl ChlorideHCID 3149543,5-diphenyl-1H-pyrazol-4-olHCID 10942334Sodium Methoxide

Product 1

HCID 213980924-(Benzyloxy)-3,5-diphenyl-1H-pyrazoleYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3,5-diphenyl-4-pyrazolol (10 g, 0.042 mole), sodium methoxide (2.27 g, 0.042 mole) and methanol (60 ml) is heated at 60°C for 2 hours. Benzyl chloride (5.33 g, 0.042 mole) is then added slowly (10 minutes) at 60°C. A white solid forms. Heating is continued overnight at 60°C. The reaction mixture is then examined by glc and found to be complete. The mixture is poured into water and the solid isolated by filtration. The solid is washed well with water and dried to yield 12.84 g (94%) product.

Workup

  1. temperatureHeating
  2. customthe solid isolated by filtration
  3. washThe solid is washed well with water
  4. customdried

Sources & evidence

ORD record
ord-d9b3c5f025394dad9f59541f17f693f5
Source dataset
uspto-grants-1976_09
Patent number
US03979409

Reaction notes

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