Ethyl 2,4-dioxovalerate → Ethyl 2-(methoxyimino)-4-oxopentanoate

HRID 251947

Reaction equation

HRID 251947 reaction equation
O=[C:2]([CH2:8][C:9](=[O:11])[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl.[CH3:13][O:14][NH2:15]>C(O)C>[CH3:13][O:14][N:15]=[C:2]([CH2:8][C:9](=[O:11])[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 69208Ethyl 2,4-dioxovalerateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 589173Ethyl 2-(methoxyimino)-4-oxopentanoateYield 45.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.5 g of ethyl 2,4-dioxovalerate, 1.45 g of O-methylhydroxylamine hydrochloride and 10 ml of ethanol was heated to reflux for 2 hours. The reaction mixture was allowed to cool to room temperature, and partitioned between water and ethyl acetate. The organic layer was washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.34 g of ethyl 2-methoxyimino-4-oxopentanoate of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f979e7f55e24e1e8910ff9a57fb6bb4
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Linked notes

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