反応 #2195515

反応方程式

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

toluene-p-sulfonic acid monohydrate

→

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

収率 95.0%

溶媒

benzene

ethylene glycol

反応条件

後処理

1. 1
   温度the solution was refluxed for 8-10 hours with a Dean-Stark apparatus
2. 2
   その他for collecting water
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   洗浄washed thoroughly with water, dilute sodium bicarbonate solution, water and finally with brine
5. 5
   乾燥The organic phase was dried over anhydrous magnesium sulfate
6. 6
   ろ過filtered
7. 7
   その他the organic solvent removed by rotary evaporator
8. 8
   その他The resultant solid was crystallized from methanol

実験手順

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).

出典