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Synthesis of hexadeuterated diethylstilbestrol ( E ‐3,4‐DI‐(4‐hydroxyphenyl) hex‐3‐ene‐1,1,1,6,6,6‐ 2 H 6 )
Author(s) -
De Clercq P. J.,
Van Peteghem C. H.,
Jonckheere J. A.,
De Leenheer A. P.
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210707
Subject(s) - chemistry , ene reaction , reagent , diethylstilbestrol , lithium (medication) , ketone , isotopomers , deuterium , medicinal chemistry , organic chemistry , medicine , biochemistry , physics , quantum mechanics , molecule , hormone , endocrinology
We describe the synthesis of deuterated diethylstilbestrol isotopomers, starting from commercially available ketones. Attempts to synthesize E ‐3,4‐di‐(4‐hydroxyphenyl) hex‐3‐ene‐2,2,5,5‐ 2 H 4 from 4‐methoxypropiophenone were not successful. Starting from 4‐methoxyacetophenone, isotopically pure E ‐3,4‐di‐(4‐hydroxyphenyl)hex‐3‐ene‐1,1,1,6,6,6‐ 2 H 6 was obtained. The 3‐steps synthesis involved alkylation of the ketone with iodomethane‐1,1,1‐ 2 H 3 , reductive coupling with titanium trichloride‐lithium reagent, and demethylation with trimethylsilyliodide. The possible use of the hexadeuterated diethylstilbestrol in isotope dilution mass spectrometry is demonstrated.