Reacción #1869194

ord-fa7e0147be2e4f0db41ecde21e4aadae

Ecuación de reacción

Clc1ccc2cccc(OCc3ccccc3)c2n1
2-chloro-8-benzyloxyquinoline
C[O-].[Na+]
NaOMe
COc1ccc2cccc(OCc3ccccc3)c2n1
oil
Rendimiento 92.0%
COc1ccc2cccc(OCc3ccccc3)c2n1
8-Benzyloxy-2-methoxyquinoline
Rendimiento 92.0%

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Temperatura
70°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe reaction solution was heated
  2. 2
    TemperaturaAfter cooling to room temperature
  3. 3
    workup.ADDITIONthe reaction solution was poured onto ice
  4. 4
    Extracciónextracted with toluene
  5. 5
    SecadoThe combined organic extracts were dried (MgSO4)
  6. 6
    Concentraciónconcentrated in vacuo

Procedimiento

The crude 2-chloro-8-benzyloxyquinoline from above was dissolved in toluene (10 mL) and added to a stirred 25 wt % solution of NaOMe in MeOH (50 mL). The reaction solution was heated with stirring overnight at 70° C. After cooling to room temperature, the reaction solution was poured onto ice and extracted with toluene. The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give a colorless oil (6.14 g, 92%). The product was used without further purification.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07498326B2uspto-grants-2009_03