Acetone → HCID 53949067, compound

Participants

Reaction Steps

Product C is seen to contain compounds of low polarity. A portion (26 g) is chromatographed on silica gel using a gradient of acetone in chloroform to separate the components. From the eluate comprising 10% acetone a fraction containing IV is obtained. This is re-chromatographed on silica gel with equal parts of hexane and ethyl acetate as eluent and provides a fraction which on recrystallising the product from aqueous ethanol gives pure IV, seen to be androsta-4,6-diene-3,17-dione, melting point 171.5°-172.5° C. (0.65 g). Similarly an eluate comprising 15% acetone is seen to contain a mixture of products, V and VI. On re-chromatography as above with hexane-ethyl acetate the compound V elutes first and on recrystallising this product from aqueous ethanol gives pure V, shown to be 12β-hydroxyandrost-4-ene-3,17-dione, melting point 169°-70° C. (8.2 g). The product VI elutes soon after and on recrystallising the product from aqueous ethanol gives pure VI, 12β-hydroxyandrosta-4,6-diene-3,17-dione, melting point 195°-6° C. (0.75 g). Similarly, an eluate comprising 20-25% acetone is seen to contain a mixture of II and VII. On re-chromatography as before, component II elutes first and then VII. On recovering this latter component and re-crystallising from aqueous ethanol gives pure VII, seen to be 12α-hydroxyandrosta-1,4-diene-3,17-dione melting point 202°-3° C. (0.34 g). Similarly the eluate comprising 30-35% acetone is seen to contain III and VIII. On re-chromatography of this product with ethyl acetate-hexane the first component eluting is VIII. On recovering this product and recrystallising from aqueous ethanol pure VIII is obtained, shown to be 7α-hydroxyandrost-4-ene-3,17-dione melting point 248°-50° C. (0.22 g). Similarly the eluate comprising 35-40% acetone is seen to contain IX and X, eluting separately. The first product is recovered and on recrystallising from aqueous ethanol pure IX is obtained shown to be 12β,17β-dihydroxyandrost-4-ene-3,17-dione melting point 118°-19° C. (1.6 g). The second product is also recovered and on recrystallising from aqueous ethanol pure X is obtained, shown to be 12β,17β-dihydroxyandrosta-1,4-diene-3-one, melting point 174°-5° C. (0.79 g).

Provenance & Evidence