
TY  - JOUR
A1  - Collins, DJ 
A1  - Hobbs, JJ 
T1  - The lability of 6-Bromo-&#916;<sup>4</sup>-3-oxosteroids: Observations on the conversion of 6&#945;- and 6&#946;-Bromocholest-4-en-3-one to 5&#945;-Cholestane-3,6-dione
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1964
VL  - 17
IS  - 6
SP  - 661
EP  - 676
KW  - 
UR  - https://doi.org/10.1071/CH9640661 
N2  - Cholesta-4,6-dien-3-one, cholest-4-ene-3,6-dione, 5&#945;-cholestane-3,6-dione, cholest-4-en-6&#946;-ol-3-one, cholest-4-en-2&#945;-ol-3-one, cholest-4-en-4-ol-3-one, and cholesta-2,5-dien-3-ol-4-one, are formed in greater or lesser amounts during chromatography of 6&#945;- and 6&#946;-bromocholest-4-en-3-one over neutral or alkaline alumina.   The conversion of 6&#945;- and 6&#946;-bromocholest-4-en-3-one to 5&#945;-cholestane-3,6-dione by the action of methanolic hydrochloric acid has been examined. The use of concentrated hydrochloric acid in this reaction afforded 3,3-dimethoxy-5&#945;-cholestan-6-one in good yield. Under similar conditions, the same ketal was also obtainable from 6&#946;-methoxycholest-4-en-3-one, cholest-4-en-6&#946;-ol-3-one, and 5&#945;-cholestane-3,6-dione.   The course of the reactions of the epimeric 6-bromocholest-4-en-3-ones with acidic ethanol, isopropanol, and t-butanol is discussed. 
ER  -

