Methanol → 3,5-Diphenyl-4-propoxy-1H-pyrazole

HRID 436608Notes

Reaction equation

HRID 436608 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.Br[CH2:25][CH2:26][CH3:27]>O>[CH2:25]([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)[CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 78401-BromopropaneHCID 3149543,5-diphenyl-1H-pyrazol-4-olHCID 10942334Sodium Methoxide

Product 1

HCID 213980993,5-Diphenyl-4-propoxy-1H-pyrazole

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. Then 1-bromopropane (5.17 g, 0.042 mole) is added slowly (5 minutes) at 60° C. The reaction mixture is then held at 60° C until the reaction is complete by tlc. The mixture is poured into water and the solid formed is isolated by filtration. Recrystallization of the solid from acetonitrile affords white crystals, 7.4 g (63%), melting point 142°-142.5° C.

Workup

  1. customis then held at 60° C until the reaction
  2. customthe solid formed
  3. customis isolated by filtration
  4. customRecrystallization of the solid from acetonitrile
  5. customaffords white crystals, 7.4 g (63%), melting point 142°-142.5° C.

Sources & evidence

ORD record
ord-98b9d69c21a14415a03e4413ff4554ff
Source dataset
uspto-grants-1977_02
Patent number
US04009277

Reaction notes

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