Reacción #2195515

Ecuación de reacción

androsta-1,4-dien-3,17-dione

toluene-p-sulfonic acid monohydrate

→

17,17-ethylenedioxyandrosta-1,4-dien-3-one

Rendimiento 95.0%

Disolventes

benzene

ethylene glycol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe solution was refluxed for 8-10 hours with a Dean-Stark apparatus
2. 2
   Otrofor collecting water
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   Lavadowashed thoroughly with water, dilute sodium bicarbonate solution, water and finally with brine
5. 5
   SecadoThe organic phase was dried over anhydrous magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Otrothe organic solvent removed by rotary evaporator
8. 8
   OtroThe resultant solid was crystallized from methanol

Procedimiento

To a solution of androsta-1,4-dien-3,17-dione (1, 10.0 g) in benzene (600 ml) and ethylene glycol (90 ml) was added toluene-p-sulfonic acid monohydrate (0.3 g), and the solution was refluxed for 8-10 hours with a Dean-Stark apparatus for collecting water. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed thoroughly with water, dilute sodium bicarbonate solution, water and finally with brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and the organic solvent removed by rotary evaporator. The resultant solid was crystallized from methanol to give 17,17-ethylenedioxyandrosta-1,4-dien-3-one (2) as a white crystalline solid in 95% yield (11.0 g).

Fuente