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Ethynylation of 17-oxo steroids labelled at position 16. synthesis of lynestrenol-16-3H at high specific activity

✍ Scribed by A. I. A. Broese; J. S. Favier; N. P. van Vliet; D. C. Warrell

Publisher
John Wiley and Sons
Year
1975
Tongue
French
Weight
345 KB
Volume
11
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The reaction of estr‐4–en‐17‐one‐16‐^2^H~2~ and 11α‐hydroxy‐estr‐4‐en‐17‐one‐16‐^2^H~2~ with potassium t‐butoxide and acetylene in tetrahydrofuran gave the 17α‐ethynyl‐17β‐ols with nearly complete loss of the label. Ethynylation with ethynyl magnesium bromide in tetrahydrofuran, however, proceeded with retention of the label. Application of the latter method to estrenone‐16‐^3^H (specific activity 14.0 Ci/mmol) gave lynestrenol‐16‐^3^H with a specific activity of 13.3 Ci/mmol.

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