Potassium Iodide → methyl [3-[2-(1,5-diphenyl-1H-pyrazol-3-yl)ethyl]phenoxy]acetate

HRID 1031956Notes

Reaction equation

HRID 1031956 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=3)[O:26][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 100428863-[2-(1,5-diphenyl-1H-pyrazol-3-yl)ethyl]phenol

Product 1

HCID 15068038methyl [3-[2-(1,5-diphenyl-1H-pyrazol-3-yl)ethyl]phenoxy]acetateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-[2-(1,5-diphenyl-1H-pyrazol-3-yl)ethyl]phenol (4.50 g, 13 mmol), methyl bromoacetate (2.23 g, 1.375 mL, 14.5 mmol), potassium carbonate (2.19 g, 16 mmol), potassium iodide (catalytic amount) and acetonitrile (80 mL) was stirred at reflux for 3 hours. The mixture was filtered, concentrated and the residue chromatographed on a column of silica gel prepared in a mixture of hexanes and diethyl ether (9:1). Subsequent elution with a mixture of hexanes and diethyl ether (1:1) furnished methyl [3-[2-(1,5-diphenyl-1H-pyrazol-3-yl)ethyl]phenoxy]acetate (4.83 g, 85% ) as an oil.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customthe residue chromatographed on a column of silica gel
  5. customprepared in a mixture of hexanes and diethyl ether (9:1)
  6. washSubsequent elution
  7. additionwith a mixture of hexanes and diethyl ether (1:1)

Sources & evidence

ORD record
ord-2a780d695cc24beebad687d672fba018
Source dataset
uspto-grants-1990_09
Patent number
US04956379

Reaction notes

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