O-Methylhydroxylamine hydrochloride → HCID 53883597, compound

HRID 1439878Notes

Reaction equation

HRID 1439878 reaction equation
O=[C:2]([CH2:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl.[CH3:16][O:17][NH2:18]>C(O)C>[CH3:16][O:17][N:18]=[C:2]([CH2:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 10998024Ethyl 2,4-dioxooctanoate

Product 1

HCID 53883597HCID 53883597, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (100 ml) solution of ethyl 2,4-dioxooctanoate (20 g) (K. Seki et al., Chem. Pharm. Bull., 32, 1568(1984)) was added, under ice-cooling, methoxyamine hydrochloride (8.4 g), and the mixture was stirred for one hour, then it was stirred for further 15 hours at room temperature. The reaction mixture was concentrated under reduced pressure, to which was added a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ether. The extract solution was dried over anhydrous sodium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel to afford the title compound as a colorless oil (16.6 g, 72%).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to which
  3. additionwas added a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionfollowed by extraction with ether
  5. dry with materialThe extract solution was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dbca3273396c410ca29bbd87004d8f6a
Source dataset
uspto-grants-1996_03
Patent number
US05496835

Reaction notes

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