Dimethyl Sulfate → Ethyl 2-methoxyimino-3,3-ethylenedioxy-4-chlorobutyrate

HRID 1982022Notes

Reaction equation

HRID 1982022 reaction equation
[OH:1][N:2]=[C:3]([C:9]1([O:15][CH2:14][CH2:13][O:12]1)[CH2:10][Cl:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:16][O:1][N:2]=[C:3]([C:9]1([O:12][CH2:13][CH2:14][O:15]1)[CH2:10][Cl:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 86738087Ethyl 2-hydroxyimino-3,3-ethylenedioxy-4-chlorobutyrate

Product 1

HCID 54025463Ethyl 2-methoxyimino-3,3-ethylenedioxy-4-chlorobutyrate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl 2-hydroxyimino-3,3-ethylenedioxy-4-chlorobutyrate (syn isomer, 0.5 g) in dried acetone (5 ml) was added potassium carbonate (0.29 g), and then dimethyl sulfate (0.265 g) was added dropwise thereto at ambient temperature with stirring. The mixture was stirred for 7 hours at ambient temperature and then filtered. The filtrate was evaporated to give ethyl 2-methoxyimino-3,3-ethylenedioxy-4-chlorobutyrate (syn isomer).

Workup

  1. stirringThe mixture was stirred for 7 hours at ambient temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b49c41d0b7a141388acdcd95e82a2419
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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