Dimethyl Sulfate → HCID 54390956, compound

HRID 1756746Notes

Reaction equation

HRID 1756746 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:9]=1[O:10][CH2:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([C:17]#[N:18])=[N:15]O.S(OC)(OC)(=O)=O>CC(C)=O>[CH3:7][C:8]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:9]=1[O:10][CH2:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([C:17]#[N:18])=[N:15][O:4][CH3:1]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 85405589HCID 85405589, compound

Product 1

HCID 54390956HCID 54390956, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (3.32 g, 0.024 mol) and acetone (200 ml) were added to 2-(2,5-dimethylphenoxymethyl)-α-hydroxyiminobenzyl cyanide (E/Z=15/85) (5.61 g, 0.02 mol). The mixture was stirred for 5 minutes. Then dimethyl sulfate (3.03 g, 0.024 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 evaporation under reduced pressure, toluene (50 ml) and 1N aqueous sodium hydroxide solution (50 ml) were added. The mixture was stirred for 1 hour. After stirring, water (150 ml) was added. The mixture was extracted with ether (150 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromarography (ethyl acetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminobenzyl cyanide (5.44 g, Yield: 92.4%, E/Z=15/85).

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. customafter evaporation under reduced pressure, toluene (50 ml) and 1N aqueous sodium hydroxide solution (50 ml)
  6. additionwere added
  7. stirringThe mixture was stirred for 1 hour
  8. stirringAfter stirring
  9. additionwater (150 ml) was added
  10. extractionThe mixture was extracted with ether (150 ml)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting residue was purified by silica gel chromarography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-838c566c5e464ac2a1c06f0c47a66973
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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