Water → HCID 53634245, compound

HRID 1069202Notes

Reaction equation

HRID 1069202 reaction equation
[CH2:1]([O:8][N:9]=[C:10]([CH2:16][CH3:17])[CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Se](=O)=[O:19].O>ClC1C=CC=CC=1>[CH2:1]([O:8][N:9]=[C:10]([CH2:16][CH3:17])[C:11](=[O:19])[C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 53867601Methyl 3-benzyloxyiminovalerate

Product 1

HCID 53634245HCID 53634245, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 47.06 g (0.2 mol) of methyl 3-benzyloxyiminovalerate in 150 ml of chlorbenzene, 24.41 g (0.22 mol) of selenium dioxide was added and the mixture was stirred for 8 hours at 120° C. After adding 200 ml of water and filtering through Celite, the filtrate was extracted three times with 200 ml of diethylether. After washing with water and a saturated aqueous sodium chloride followed by drying over with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain a residue, which was purified by a column chromatography on a silica gel (n-hexane/ethyl acetate) to obtain 31.15 g (yield 62%) of methyl 3-benzyloxyimino-2-oxovalerate as a colorless oil.

Workup

  1. filtrationfiltering through Celite
  2. extractionthe filtrate was extracted three times with 200 ml of diethylether
  3. washAfter washing with water
  4. dry with materialby drying over with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain a residue, which
  7. customwas purified by a column chromatography on a silica gel (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-58b2e96176024aedbbaab82bf58d5ce8
Source dataset
uspto-grants-2001_06
Patent number
US06251949B1

Reaction notes

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