Diethyl Sulfate → HCID 54272823, compound

HRID 1699148Notes

Reaction equation

HRID 1699148 reaction equation
[CH3:1][C:2](=[CH2:10])[CH2:3][C:4](=[N:8][OH:9])[C:5](=[O:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:21][CH3:22])(=O)=O>CC(C)=O>[CH2:21]([O:9][N:8]=[C:4]([CH2:3][C:2]([CH3:1])=[CH2:10])[C:5](=[O:7])[CH3:6])[CH3:22]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 73447335HCID 73447335, compound

Product 1

HCID 54272823HCID 54272823, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
23 °C

Procedure

285.7 g of 5-methylhex-5-ene-2,3-dione 3-oxime from Example 1 were dissolved in 750 ml of acetone and admixed with 335.8 g of potassium carbonate. 362 g of diethyl sulfate in 300 ml of acetone were then added dropwise, and the mixture was stirred at 23° C. for 2 hours. The solvent was subsequently removed under reduced pressure, the residue was taken up in methyl tert-butyl ether/water and the aqueous phase was extracted again 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 355.4 g of the title compound as a yellow oil.

Workup

  1. customThe solvent was subsequently removed under reduced pressure
  2. extractionthe aqueous phase was extracted again 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-75504b453c874d2da164bea9a48c1731
Source dataset
uspto-grants-2002_02
Patent number
US06344589B1

Reaction notes

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