Diethyl Sulfate → HCID 21090999, compound

HRID 351254Notes

Reaction equation

HRID 351254 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([OH:28])[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:35](OS(OCC)(=O)=O)[CH3:36]>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([O:28][CH2:35][CH3:36])[CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 178492087HCID 178492087, compound

Product 1

HCID 21090999HCID 21090999, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 5-[4-(benzyloxy)phenyl]-3-hydroxy-1-(4-methoxyphenyl)-1H-pyrazole 2.0 g and K2CO3 2.23 g in DMSO 20 ml was added diethylsulfate 1.24 g. After stirring at ambient temperature for 2 hours, the reaction was quenched by adding 28% aqueous ammonium hydroxide solution and ice. The mixture was partitioned between AcOEt and H2O. The organic layer was washed with H2O and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=40% and the solvent was evaporated in vacuo. The reisual solid was recrystallized from IPE to give 5-[4-(benzyloxy)phenyl]-3-ethoxy-1-(4-methoxy-phenyl)-1H-pyrazole 1.44 g as a powder.

Workup

  1. customthe reaction was quenched
  2. additionby adding 28% aqueous ammonium hydroxide solution and ice
  3. customThe mixture was partitioned between AcOEt and H2O
  4. washThe organic layer was washed with H2O and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluted with AcOEt/n-hexane=40%
  9. customthe solvent was evaporated in vacuo
  10. customThe reisual solid was recrystallized from IPE

Sources & evidence

ORD record
ord-590aa8057f6c4ec0aafd570846edf1ec
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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