Dimethyl Sulfate → Tert-butyl 2-methoxyimino-3-oxobutyrate

HRID 1632721Notes

Reaction equation

HRID 1632721 reaction equation
[C:1]([O:5][C:6](=[O:13])[C:7](=[N:11][OH:12])[C:8]([CH3:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].S(OC)(O[CH3:18])(=O)=O>O.CO>[C:1]([O:5][C:6](=[O:13])[C:7](=[N:11][O:12][CH3:18])[C:8]([CH3:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6497Dimethyl SulfateHCID 178468384CID 71354250

Product 1

HCID 54110352Tert-butyl 2-methoxyimino-3-oxobutyrate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 215 g of Na2CO2 in 2200 ml of water is added at room temperature a solution of 128 g of 2-hydroxyiminoacetoacetic acid-tert.butyl ester in 475 ml of methanol. 255 g of dimethyl sulphate are added, dropwise, at 8°-10°, and after 3 hours at 8°-10° and 15 hours at room temperature, the mixture is filtered. The filtrate is extracted 3 times with ethyl acetate extracted 3 times with ethyl acetate, dried over magnesium sulphate and evaporated to obtain the heading compound.

Workup

  1. filtration15 hours at room temperature, the mixture is filtered
  2. extractionThe filtrate is extracted 3 times with ethyl acetate
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto obtain the heading compound

Sources & evidence

ORD record
ord-6f9800a5172f431f972a01507faa2025
Source dataset
uspto-grants-1984_10
Patent number
US04477448

Reaction notes

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