Collect. Czech. Chem. Commun. 1998, 63, 549-556

Preparation of Steroid Olefins from Heptafluorobutyrates

Lucie Dalibová and Ladislav Kohout

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic,166 10 Prague 6, Czech Republic


Steroids with hydroxyl group in positions 2, 3, 6, 7, 17 and 20 were esterified with heptafluorobutyric anhydride. The obtained esters on treatment with lithium bromide in N,N-dimethylacetamide in the presence of pyridinium tosylate afforded the corresponding olefins in high yields.

Keywords: Steroids; Heptafluorobutyrates; Elimination; Olefins; NMR spectroscopy; Solvolysis.