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

HRID 598192

Reaction equation

HRID 598192 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.ClCCl>[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

5

Reactant 2

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

Product 1

HCID 589173Ethyl 2-(methoxyimino)-4-oxopentanoateYield 143.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2,4-dioxopentanoate (10.9 g, 68.7 mmol) and N-methoxyamine hydrochloride (4.01 g, 48.1 mmol) in ethanol (40 ml) was left to stand over molecular sieves 3A (25 g) for 18 h and diluted with dichloromethane (25 ml) The sieves was removed by filtration and the filtrate was concentrated under vacuum. The residue was purified by silica gel chromatography eluting with 5% ethyl acetate/n-hexane to give the title compound (12.9 g, 34%).

Workup

  1. waitwas left
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 5% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-b4b1ee3a41174507ba3942db2b2a29f1
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Linked notes

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