Dimethyl Sulfate → 2-Phenoxy-alpha-methoxyiminobenzyl cyanide

HRID 1779728Notes

Reaction equation

HRID 1779728 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[O:7]([C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[C:16]([C:19]#[N:20])=[N:17]O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.S(OC)(OC)(=O)=O>CC(C)=O>[O:7]([C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[C:16]([C:19]#[N:20])=[N:17][O:4][CH3:1])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 853212152-Phenoxy-alpha-hydroxyiminobenzyl cyanide

Product 1

HCID 541653652-Phenoxy-alpha-methoxyiminobenzyl cyanideYield 108.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (3.11 g, 0.023 mol) and acetone (60 ml) were added to 2-phenoxy-α-hydroxyiminobenzyl cyanide (E/Z=11/89)(7.15 g, 0.03 mol). The mixture was stirred for 5 minutes. Then dimethyl sulfate (5.68 g, 0.045 mol) was added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the resulting insoluble materials were removed. To the residue obtained after concentration under reduced pressure, toluene (60 ml) and 1N aqueous sodium hydroxide solution (60 ml) were added. The mixture was stirred at room temperature for 1 hour. After stirring, water (60 ml) was added. The mixture was extracted with toluene (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-phenoxy-α-methoxyiminobenzyl cyanide (6.28 g, Yield: 83.0%, E/Z=7/93).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customAfter completion of the reaction
  3. customthe resulting insoluble materials were removed
  4. customTo the residue obtained
  5. concentrationafter concentration under reduced pressure, toluene (60 ml) and 1N aqueous sodium hydroxide solution (60 ml)
  6. additionwere added
  7. stirringThe mixture was stirred at room temperature for 1 hour
  8. stirringAfter stirring
  9. additionwater (60 ml) was added
  10. extractionThe mixture was extracted with toluene (100 ml)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-99f4c2b7c4b842d1ab5fd9e0e298c4e9
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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