Reaktion #1379895

ord-175dfcd48372445b9432998d273d61af

Reaktionsgleichung

C=CC(=O)Cl
acryloyl chloride
Cl.NOCc1ccccc1
O-benzyl hydroxylamine hydrochloride
O
Water
C=CC(=O)NOCc1ccccc1
N-benzyloxyacrylamide

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe layers were separated
  2. 2
    WaschenThe organic solution was washed with diluted hydrochloric acid
  3. 3
    TrocknenThe organic layer was dried over magnesium sulfate
  4. 4
    Filtrationfiltered
  5. 5
    Sonstigethe solvent removed under reduced pressure
  6. 6
    SonstigeThe residue was purified by flash chromatography
  7. 7
    workup.ADDITIONa mixture of hexane and ethyl acetate
  8. 8
    SonstigeThe purification

Vorschrift

A solution of acryloyl chloride dissolved in dry dichloromethane was cooled at 0° C. with an ice bath. A mixture of O-benzyl hydroxylamine hydrochloride (29) and N,N-diisopropylethylaamine in dry dichloromethane was added. Water was added and the layers were separated. The organic solution was washed with diluted hydrochloric acid, a saturated sodium bicarbonate solution, water, and brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was purified by flash chromatography using a mixture of hexane and ethyl acetate. The purification gave N-benzyloxyacrylamide (30).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07238339B2uspto-grants-2007_07