Reacción #487538

ord-ca611b5c5ba04339a7d021a1bbd71ce8

Ecuación de reacción

O
water
CNOC.Cl
N,O-dimethylhydroxyamine hydrochloride
CCCCCCCCCC(=O)O
Decanoic acid
CCCCCCCCCC(=O)N(C)OC
N-methoxy-N-methyldecanamide
Rendimiento 97.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwas then added to the solution
  2. 2
    workup.STIRRINGthe obtained mixture was further stirred for 3 hours
  3. 3
    Extracciónthe reaction solution was extracted with dichloromethane two times
  4. 4
    workup.ADDITIONAnhydrous magnesium sulfate was added to the organic layer
  5. 5
    Otroto dry it
  6. 6
    Filtraciónthe resultant was filtrated
  7. 7
    Concentraciónwas then concentrated
  8. 8
    OtroThe obtained residue was purified

Procedimiento

Decanoic acid (4 g, 23.2 mmol) was dissolved in an anhydrous dichloromethane solution (80 mL), and 1,1-carbonyldiimidazole (4.5 g, 27.9 mmol) was then added to the solution, followed by stirring for 1.5 hours. Subsequently, N,O-dimethylhydroxyamine hydrochloride (2.7 g, 27.9 mmol) was added to the reaction solution, and the obtained mixture was further stirred for 3 hours. After addition of distilled water, the reaction solution was extracted with dichloromethane two times. Anhydrous magnesium sulfate was added to the organic layer to dry it, and the resultant was filtrated and was then concentrated. The obtained residue was purified using column chromatography (hexane:ethyl acetate=8:1), so as to obtain N-methoxy-N-methyldecanamide (4.8 g, 97%) as an amide body in the form of a colorless transparent liquid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08741871B2uspto-grants-2014_06