Reacción #7972

Ecuación de reacción

indans

6-methoxy-1-propyl-indan

KMnO4

→

5-methoxy-3-propyl-1-indanone

Rendimiento 15.1%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting mixture was heated
2. 2
   Temperaturaat reflux for 89 hours
3. 3
   Filtraciónfiltered through a celite pad
4. 4
   SecadoThe filtrate was dried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated under vacuum to an oil (1.155 g)
7. 7
   OtroThe crude product was purified by chromatography on a Biotage FLASH 12M column
8. 8
   Lavadoeluting with 10% EtOAc in hexanes

Procedimiento

The mixture of indans from step 2 (1.287 g, approx. 6.1 mmol) in CH2Cl2 (50 mL) was treated with a finely ground mixture of KMnO4 (7.00 g) and CuSO4.xH2O. The resulting mixture was heated at reflux for 89 hours, then cooled to room temperature and filtered through a celite pad. The filtrate was dried over MgSO4, filtered and evaporated under vacuum to an oil (1.155 g). The crude product was purified by chromatography on a Biotage FLASH 12M column, eluting with 10% EtOAc in hexanes, to afford 5-methoxy-3-propyl-1-indanone (0.188 g) as an oil. Other column fractions afforded 6-methoxy-3-propyl-1-indanone, the indan starting materials, and 5-methoxy-1-indanone.

Fuente