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Preparation of pentadeuterated diethylstilbestrol ([1, 1, 1, 2, 2‐D 5 ] E‐3, 4‐di‐(4‐hydroxyphenyl)‐hex‐3‐ene)
Author(s) -
Metzler Manfred
Publication year - 1978
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.2580150118
Subject(s) - diethylstilbestrol , chemistry , ene reaction , bromide , bromine , medicinal chemistry , butyraldehyde , magnesium , magnesium bromide , organic chemistry , catalysis , biochemistry , hormone
[1, 1, 1, 2, 2‐D 5 ] E‐3, 4‐Di‐(4‐hydroxyphenyl)‐hex‐3‐ene has been synthesized from 1, 1‐di‐(4‐benzyloxyphenyl)‐butyraldehyde. The preparation of this aldehyde is described. Its reaction with pentadeuterated ethyl magnesium bromide yields [1,1,1,2,2‐D 5 ] 4,4‐di‐(4‐benzyloxyphenyl)‐hexan‐3‐ol, which is debenzylated by catalytical hydrogenation. Upon heating of the resulting [1,1,1,2,2‐D 5 ] 4,4‐di‐(4‐hydroxyphenyl)‐hexan‐3‐ol, a mixture of pentadeuterated diethylstilbestrol and pentadeuterated pseudo diethylstilbestrol is formed, from which the pentadeuterated diethylstilbestrol is obtained in pure form through fractional crystallization.