반응 #357801

반응 방정식

Sodium borohydride

3,3-ethylenedioxyestra-5(10), 9(11)-dien-17-one

sodium chloride

acetone

→

expected product

3,3-ethylenedioxyestra-5(10), 9(11)-dien-17-ol

용매

sodium hydroxide

methanol

ethyl acetate

water

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture is stirred for 1 h
2. 2
   기타The mixture is separated
3. 3
   추출the aqueous phase is re-extracted with ethyl acetate
4. 4
   세척The combined organic phases are washed with water
5. 5
   건조dried over sodium sulfate
6. 6
   농축concentrated at normal pressure to 500 ml
7. 7
   workup.DISTILLATIONThe distillation
8. 8
   온도while maintaining the volume constant by gradual introduction of 1,2-dimethoxyethane (DME)
9. 9
   기타is 83° C
10. 10
    추출a dry extract

실험 절차

Sodium borohydride (MW=37.8; 18.9 g; 500 mmol) in solution in 0.5 N sodium hydroxide (100 ml) is introduced, over approximately 5 min at around 2° C., into a suspension of 3,3-ethylenedioxyestra-5(10), 9(11)-dien-17-one (MW=314.4; 100 g; 318 mmol) in methanol (1 liter). The mixture is stirred for 2 h at around 2° C. and then acetone (100 ml) is introduced over approximately 15 min at around 5° C. The mixture is stirred for 1 h and the medium is run, at around 20° C., into a stirred mixture of water (2 liters), sodium chloride (500 g) and ethyl acetate (400 ml). The mixture is separated by settling out and the aqueous phase is re-extracted with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and concentrated at normal pressure to 500 ml. The distillation is continued while maintaining the volume constant by gradual introduction of 1,2-dimethoxyethane (DME). The temperature at the end of exchange is 83° C. The solution is used as it is in the subsequent stage, but a dry extract results in the expected product (resin). C20H28O3; MW=316.4:

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