Dimethyl Sulfate → HCID 54346298, compound

HRID 2228843Notes

Reaction equation

HRID 2228843 reaction equation
[CH3:1][C:2](=[CH2:10])[CH2:3][C:4](=[N:8][OH:9])[C:5](=[O:7])[CH3:6].[C:11](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:11][O:9][N:8]=[C:4]([CH2:3][C:2]([CH3:1])=[CH2:10])[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 73447335HCID 73447335, compound

Product 1

HCID 54346298HCID 54346298, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
23 °C

Procedure

141 g of 5-methylhex-5-ene-2,3-dione 3-oxime from Example 1 were dissolved in 750 ml of acetone and admixed with 165.6 g of potassium carbonate. 145 g of dimethyl sulfate in 100 ml of acetone were then added dropwise, and the mixture was stirred at 23° C. for 4 hours. The solvent was then removed under reduced pressure, the residue was taken up in methyl tert-butyl ether/water and the aqueous phase was extracted repeatedly with methyl tert-butyl ether. The combined organic phases were washed with 15% strength ammonia solution and water and dried over sodium sulfate, and the solvent was removed under reduced pressure. This gave 141 g of the title compound as a yellow oil.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. extractionthe aqueous phase was extracted repeatedly with methyl tert-butyl ether
  3. washThe combined organic phases were washed with 15% strength ammonia solution and water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8c2576f1c1024a5eaea3aca0da6d1d41
Source dataset
uspto-grants-2002_07
Patent number
US06417388B1

Reaction notes

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