Reacción #833521

Ecuación de reacción

THF

4a

1,4-dimethoxy-6,7,10,11-tetrakis(decyloxy)triphenylene

→

5a

Rendimiento 80.0%

6,7,10,11-tetrakis(decyloxy)triphenylene-1,4-dione

Rendimiento 80.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with a saturated solution of NaHCO3 and water
2. 2
   SecadoThe organic layer was dried with MgSO4
3. 3
   Otrothe solvent removed under reduced pressure
4. 4
   OtroThe crude product was purified by column chromatography on silica gel (1:1 CH2Cl2/hexane)

Procedimiento

An aqueous solution (1 mL) of (NH4)2Ce(NO3)6 (0.035 g, 0.064 mmol) was added dropwise to a THF solution (5 mL) of 4a (0.029 g, 0.032 mmol). The reaction mixture immediately turned deep red. After 6 h the reaction mixture was poured into ether and washed with a saturated solution of NaHCO3 and water. The organic layer was dried with MgSO4 and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel (1:1 CH2Cl2/hexane) to afford 5a as a deep red solid in 80% yield (mp 86-87° C.).

Fuente