Benzyloxyamine hydrochloride → Methyl 3-benzyloxyiminovalerate

HRID 1069201Notes

Reaction equation

HRID 1069201 reaction equation
[C:1]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=O)[CH2:2][CH3:3].Cl.[CH2:11]([O:18][NH2:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[K+]>CO.O>[CH2:11]([O:18][N:19]=[C:1]([CH2:2][CH3:3])[CH2:5][C:6]([O:8][CH3:9])=[O:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 121699Methyl 3-oxovalerateHCID 517044Potassium Acetate

Product 1

HCID 53867601Methyl 3-benzyloxyiminovalerateYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 26.03 g (0.2 mol) of methyl propionylacetate in 300 ml of methanol, 100 ml of water and 35.12 g (0.22 mol) of benzyloxyamine hydrochloride, 19.69 g (0.24 mol) of potassium acetate were added and the mixture was stirred for 15 hours at room temperature. After distilling methanol off under reduced pressure, followed by adding 200 ml of water and extracting three times with 200 ml of ethyl acetate, the mixture was washed with water and a saturated aqueous sodium chloride and then dried over with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 47.06 g (yield: 100%) of a crude methyl 3-benzyloxyiminovalerate as a colorless oil.

Workup

  1. distillationAfter distilling methanol off under reduced pressure
  2. additionby adding 200 ml of water
  3. extractionextracting three times with 200 ml of ethyl acetate
  4. washthe mixture was washed with water
  5. dry with materiala saturated aqueous sodium chloride and then dried over with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a3d1bad506d64614a6e056427c78e6f0
Source dataset
uspto-grants-2001_06
Patent number
US06251949B1

Reaction notes

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