Dimethyl Sulfate → HCID 22051434, compound

HRID 1840667Notes

Reaction equation

HRID 1840667 reaction equation
CC(=O)[C:3](=NO)[C:4](=[O:6])[CH3:5].S(OC)(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(NCC)C.[CH3:28][O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>CC(C)=O>[CH3:28][O:29][C:30]([CH3:33])([CH3:32])[CH3:31].[CH3:3][C:4]([CH3:5])=[O:6]

Participants

7

Reactant 5

HCID 6497Dimethyl SulfateHCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl ether2×HCID 178468373HCID 178468373, compound

Product 1

HCID 22051434HCID 22051434, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 12.9 g of pentane-2,3,4-trione 3-oxime in 38.5 g of MTBE and 13.9 g of dimethyl sulfate (DMS) were added dropwise to a suspension of 16.6 g of potassium carbonate in a mixture of 30 g of tert-butyl methyl ether (MTBE) and 10 g of acetone at about 20° C. with cooling. After stirring at about 20° C. for 2 h, 2.2 g of diethylamine were added to destroy excess DMS and, after stirring at about 20° C. for a further hour, 80 ml of water were added. The solution was extracted with tert-butyl methyl ether. From the combined organic phases there were obtained after washing with 1 N H2SO4 11 g of pentane-2,3,4-trione 3-O-methyloxime (85.8% pure according to GC analysis), corresponding to a yield of 70.0% of theory.

Workup

  1. temperaturewith cooling
  2. customto destroy excess DMS
  3. stirringafter stirring at about 20° C. for a further hour
  4. addition80 ml of water were added
  5. extractionThe solution was extracted with tert-butyl methyl ether
  6. customFrom the combined organic phases there were obtained
  7. washafter washing with 1 N H2SO4 11 g of pentane-2,3,4-trione 3-O-methyloxime (85.8% pure according to GC analysis), corresponding to a yield of 70.0% of theory

Sources & evidence

ORD record
ord-58949d51116e4e109dbab0bca7bf0ed9
Source dataset
uspto-grants-2004_01
Patent number
US06680410B2

Reaction notes

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