Reaktion #362249

Reaktionsgleichung

water

2-iodo-1α-methyl-androst-4-ene-3,17-dione

crude product

2-iodo-1α-methyl-androst-4-ene-3,17-dione

lithium carbonate

→

1-Methyl-androsta-1,4-diene-3,17-dione

Lösungsmittel

N-methyl-pyrrolidone

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling of the reaction solution it
2. 2
   Extraktionthe product is extracted 3 times with 450 ml of ethyl acetate
3. 3
   TrocknenThe combined ethyl acetate phases are dried on sodium sulfate
4. 4
   Einengenconcentrated by evaporation
5. 5
   SonstigeThe residue is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent
6. 6
   EinengenAfter concentration
7. 7
   Sonstigeby evaporation of the fractions and recrystallization of the substance from ethyl acetate, 6.9 g of 1-methyl-androsta-1,4-diene-3,17-dione (69% of theory over 2 stages relative to 1α-methyl-androst-4-ene-3,17-dione in example 7) of melting point 168°-169° C.
8. 8
   Sonstigeis obtained

Vorschrift

14.9 g of 2-iodo-1α-methyl-androst-4-ene-3,17-dione crude product of example 7 and 4.73 g (64 mmol) of anhydrous lithium carbonate are stirred in 95 ml of N-methyl-pyrrolidone for 1 hour at 130° C. under nitrogen atmosphere. After cooling of the reaction solution it is added to 0.6 1 of water and the product is extracted 3 times with 450 ml of ethyl acetate. The combined ethyl acetate phases are dried on sodium sulfate and then concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane as mobile solvent. After concentration by evaporation of the fractions and recrystallization of the substance from ethyl acetate, 6.9 g of 1-methyl-androsta-1,4-diene-3,17-dione (69% of theory over 2 stages relative to 1α-methyl-androst-4-ene-3,17-dione in example 7) of melting point 168°-169° C. is obtained.

Quelle