Reacción #2471752

ord-e507d3be30af438188edc2457d9b44c0

Ecuación de reacción

O=Cc1ccc(O)c2ccccc12
4-hydroxy-1-naphtaldehyde
CC1=CC(=C(C#N)C#N)C=C(C)O1
4-(dicyanomethylene)-2,6-dimethyl-4H-pyrane
C1CCNCC1
piperidine
CC1=CC(=C(C#N)C#N)C=C(/C=C/c2ccc(O)c3ccccc23)O1
desired compound
Rendimiento 48.2%
CC1=CC(=C(C#N)C#N)C=C(/C=C/c2ccc(O)c3ccccc23)O1
((E)-2-(2-(4-hydroxynaphthalene-1-yl)vinyl)-6-methyl-4H-pyrane-4-ylidene)malononitrile
Rendimiento 48.2%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe resultant was heated
  2. 2
    Temperaturarefluxed under an argon atmosphere for 6 hours
  3. 3
    Otrothe solvent was removed under reduced pressure
  4. 4
    Otrofollowed by purification by column chromatography (SiO2, CHCl3:MeOH=10:1 (v/v))

Procedimiento

4-hydroxy-1-naphtaldehyde (0.70 g (5.81 mmol)), 4-(dicyanomethylene)-2,6-dimethyl-4H-pyrane (1.0 g (5.81 mmol)), piperidine (0.50 g (5.81 mmol)), and ethanol (50 mL) were added to a 50-mL three-neck flask. The resultant was heated and refluxed under an argon atmosphere for 6 hours and then the solvent was removed under reduced pressure, followed by purification by column chromatography (SiO2, CHCl3:MeOH=10:1 (v/v)). Thus a desired compound was obtained (yield: 48.2%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08263791B2uspto-grants-2012_09