Reacción #1379895

ord-175dfcd48372445b9432998d273d61af

Ecuación de reacción

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

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07238339B2uspto-grants-2007_07