Reacción #1209

ord-c54f235e113e4ef68f3a56e016403a66

Ecuación de reacción

OCCCCCCCCCCCCCCC1CO1
1,2-epoxy-16-hexadecanol
NCCO
ethanolamine
N#N
N2
NCCO
ethanolamine
OCCCCCCCCCCCCCCC(O)CNCCO
title compound
Rendimiento 68.0%
OCCCCCCCCCCCCCCC(O)CNCCO
1-(2-hydroxyethylamino)-2,16-hexadecanediol
Rendimiento 68.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroA 50-ml two-necked flask equipped with a stirrer
  2. 2
    TemperaturaWhile heating
  3. 3
    workup.DISTILLATIONwere distilled off under reduced pressure
  4. 4
    Otrothe resultant residue was purified by flash column chromatography on silica gel

Procedimiento

A 50-ml two-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 4.14 g (68 mmol) of ethanolamine and 0.8 g of ethanol. While heating and stirring the mixture at 80° C. in an N2 atmosphere, an ethanol solution of 0.87 g (3.4 mmol) of 1,2-epoxy-16-hexadecanol was added dropwise over 1.5 hours. The resultant mixture was stirred further for 2 hours at 80° C. After completion of the reaction, ethanol and excess ethanolamine were distilled off under reduced pressure, and the resultant residue was purified by flash column chromatography on silica gel, thereby obtaining 0.72 g (yield: 68%) of the title compound (IId-1).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723497uspto-grants-1998_03