Water → HCID 53698905, compound

HRID 977061Notes

Reaction equation

HRID 977061 reaction equation
Cl.[CH3:2][O:3][NH2:4].C(=O)([O-])[O-].[K+].[K+].[C:11]1([C:17](=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CN(C)C=O>[CH3:2][O:3][N:4]=[C:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15349Ethyl benzoylformateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 53698905HCID 53698905, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1.4 g (16.8 mmol) of O-methylhydroxylamine hydrochloride and 1.16 g (8.4 mmol) of potassium carbonate were added to a solution of 0.50 g (2.8 mmol) of ethyl phenylglyoxylate in N,N-dimethylformamide, and the resulting mixture was stirred at 90° C. for 4 hours. At the end of this time, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by column chromatography through silica gel, eluted with a stepwise gradient of ethyl acetate (10-30%) in hexane, to give 0.47 g (67% yield) of the less polar isomer of the title compound and 0.13 g (19% yield) of the more polar isomer of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by column chromatography through silica gel
  6. washeluted with a stepwise gradient of ethyl acetate (10-30%) in hexane

Sources & evidence

ORD record
ord-bff755ab6eed4a95ab482b12dbe6b7ce
Source dataset
uspto-grants-1997_03
Patent number
US05614470

Reaction notes

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