반응 #684538

반응 방정식

water

acetic acid

potassium borohydride

potassium borohydride

potassium borohydride

19-hydroxyandrost-4-en-3-one

→

17β,19-dihydroxyandrost-4-en-3-one

용매

ethanol

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   workup.ADDITIONis added
3. 3
   workup.DISTILLATIONThe ethanol is distilled off under reduced pressure
4. 4
   여과The solid which separates is filtered off
5. 5
   기타dried
6. 6
   workup.DISSOLUTIONdissolved in 25 liters of hot chloroform after which the temperature
7. 7
   기타is adjusted to 25° C
8. 8
   workup.ADDITIONTo the chloroform solution is added 250 g of manganese dioxide
9. 9
   workup.STIRRINGthe mixture is stirred for two hours
10. 10
    여과then filtered
11. 11
    기타the solvents removed under reduced pressure
12. 12
    기타The solid residue is recrystallized from acetonitrile

실험 절차

A solution of 150 g of 19-hydroxyandrost-4-en-3-one in 6 liters of ethanol is cooled in an ice bath. To this cold solution is added 13.5 g of potassium borohydride, and the reaction mixture is stirred for two hours at about 0° C after which a second 13.5 g or potassium borohydride is added. Two hours later a third 13.5 g portion of potassium borohydride is added to the reaction mixture which is stirred for an additional one hour then poured into 11 liters of water to which 70 ml of acetic acid is added. The ethanol is distilled off under reduced pressure and the aqueous residue cooled to 0° C. The solid which separates is filtered off, dried and dissolved in 25 liters of hot chloroform after which the temperature is adjusted to 25° C. To the chloroform solution is added 250 g of manganese dioxide, and the mixture is stirred for two hours then filtered and the solvents removed under reduced pressure. The solid residue is recrystallized from acetonitrile to give 17β,19-dihydroxyandrost-4-en-3-one. M.P. 205°-207° C.

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