Abstract
ABOUT a year ago, we published a method whereby it was possible to carry out a practically quantitative addition of acetylene to irans-dehydro-androsterone1. We have in the meantime ascertained that the thereby easily obtained 17-ethinyl-3-trans, 17-dioxy-androstene-(5), [A], in glacial acetic acid in the presence of acetic anhydride and mercuric oxide together with the boro fluoride-ether catalyst2 readily adds on acetic acid to the triple bond and gives rise to 20-acetoxy-3-trans, 17-dioxy-pregnadiene-(5, 20), [B], m.p. 175–177° (corr.); CH-determinations agree with C23H34O4 The 3-monoacetate of [A] also adds on acetic acid with the formation of 3-trans, 20-diacetoxy-17-oxy-pregnadiene-(5,20), [C], m.p. 191–192° (corr.); CH-determinations agree with C25H36O5
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References
Ruzicka, L., and Hofmann, K., Helv. chim. Acta, 20, 1280 (1937).
Hennion, G. F., Hinton, H., and Nieuwland, J. A., J. Amer. Chem. Soc., 55, 2858 (1933).
In collaboration with Prof. Reichstein.
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RUZICKA, L., MELDAHL, H. A Simple Conversion of Trans-Dehydro-Androsterone into Pregnane Derivatives. Nature 142, 399 (1938). https://doi.org/10.1038/142399a0
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DOI: https://doi.org/10.1038/142399a0
