Dimethyl Sulfate → 3(2H)-Benzofuranone, O-methyloxime

HRID 612810Notes

Reaction equation

HRID 612810 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=[N:10][OH:11])[CH2:2]1.[H-].[Na+].S(OC)(O[CH3:18])(=O)=O>O>[CH3:18][O:11][N:10]=[C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][CH2:2]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 73014405Benzofuran-3-one oxime

Product 1

HCID 542716163(2H)-Benzofuranone, O-methyloximeYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.7 g of benzofuran-3-one oxime are dissolved in 15 ml of dimethylfornamide. At 20° C., 1 g of sodium hydride (60%) is added and the mixture is stirred until the evolution of gas ceases. 3.15 g of dimethyl sulphate are then added dropwise and the mixture is stirred at 20° C. for 24 hours. The reaction mixture is poured into water, extracted with ethyl acetate, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. The residue is chromatographed over silica gel using n-hexane/acetone (4:1). 1.7 g (42% of theory) of benzofuran-3-one O-methyl-oxime are obtained as an oil.

Workup

  1. stirringthe mixture is stirred at 20° C. for 24 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-1b10c105bb60410db8a8b210609ec1a6
Source dataset
uspto-grants-1999_12
Patent number
US06005104

Reaction notes

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