Reacción #56594

ord-7b03299eb0ab4ce5adf307e56e52b766

Ecuación de reacción

Cc1cc(N=Nc2ccc(N=Nc3ccccc3)cc2)ccc1O
4-hydroxy-3-methyl4′-phenylazo-azobenzene
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CCOC(=O)N=NC(=O)OCC
diethyl azodicarboxylate
C=CC(=O)OCCCCO
4-hydroxybutylacrylate
C=CC(=O)OCCCCOc1ccc(N=Nc2ccc(N=Nc3ccccc3)cc2)cc1C
4-(4-Acryloyloxybutyloxy)-3-methyl-4′-phenylazo-azobenzene

Disolventes

Condiciones de reacción

Temperatura
-30°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONAfter complete addition
  2. 2
    Concentraciónconcentrated to dryness
  3. 3
    FiltraciónThe obtained yellow-red residue was purified by filtration on silica
  4. 4
    Otroto give 0.65 g of pure yellow-orange crystalys

Procedimiento

To a solution of 0.63 g of 4-hydroxy-3-methyl4′-phenylazo-azobenzene, 1.05 g of triphenylphosphine and 0.58 g of 4-hydroxybutylacrylate in 10 ml THF; which was cooled to −30° C., was added dropwise a solution of 0.70 g of diethyl azodicarboxylate in 5 ml THF. After complete addition, the reaction mixture was stirred for further 45 min at room temperature, and then concentrated to dryness. The obtained yellow-red residue was purified by filtration on silica using methylenechloride as the eluent to give 0.65 g of pure yellow-orange crystalys; λmax. (CB 483): 395 nm.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07419620B2uspto-grants-2008_09