TESTOSTERONE HEPTAFLUOROBUTYRATES . DERIVATIVES FOR GAS CHROMATOGRAPHY

The reaction of testosterone with heptafluorobutyric anhydride, in the presence of pyridine or collidine, leads to two diheptafluorobutyrate (HFB) derivatives. These compounds are believed to be the di-HFB esters of 2,4-androstadien-3, 17β-diol (A) and 3, 5-androstadien-3, 17β-diol (B), with A as the major product. This is similar to the reaction with silylating reagents which leads to two isomeric enol ethers. In benzene or acetone solution, and in the absence of an organic base, the same two isomers are formed, but with B as the major product. Although the latter reaction has been recommended for quantitative work, the formation of isomeric enol esters has not been noted. Since the products are not stable in the reaction medium, the method is not entirely satisfactory. The reaction in pyridine solution should be suitable for quantitative work; the products are stable in solution and can be detected in subnanogram amounts. © 1969, Taylor & Francis Group, LLC. All rights reserved.