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Ethynylation of 17‐oxo steroids labelled at position 16. synthesis of lynestrenol‐16‐ 3 H at high specific activity
Author(s) -
Broese A. I. A.,
Favier J. S.,
van Vliet N. P.,
Warrell D. C.
Publication year - 1975
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590110207
Subject(s) - tetrahydrofuran , bromide , chemistry , lynestrenol , medicinal chemistry , potassium , magnesium bromide , acetylene , magnesium , medicine , organic chemistry , research methodology , population , environmental health , solvent , family planning
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.