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Preparation of pentadeuterated diethylstilbestrol ([1, 1, 1, 2, 2-D5] E-3, 4-di-(4-hydroxyphenyl)-hex-3-ene)

✍ Scribed by Manfred Metzler

Publisher
John Wiley and Sons
Year
1978
Tongue
French
Weight
390 KB
Volume
15
Category
Article
ISSN
0022-2135

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✦ Synopsis

1,1,1,2,2-D, ] E-3,4-Di-(4-hydroxyphenyl) -hex-3-ene has been synthesized from l,l-di-(4-benzyloxyphenyl)-butyraldehyde. The preparation of this aldehyde is described. Its reaction with pentadeuterated ethyl magnesium bromide yields [ 1 , 1 , 1 , 2 , 2-D5] 4,4-d1-(4-benzyloxyphenyl)-hexan-3-01, which I s debenzylated by catalytical hydrogenation. Upon heating of the resulting [I I 1 , I , 2,2-D,] 4,4-di-(4-hydroxyphenyl) -hexan-3-01, a mixture of pentadeuterated diethylstilbestrol and pentadeuterated pseudo diethylstilbestrol is formed, from which the pentadeuterated diethylstilbestrol is obtained in pure form through fractional crystallization. * This work was supported by the Deutsche Forschungsgemeinschaft. The interest and support of Prof. H.-G. Neumann and the skilful technical assistance of Mrs. Hella Raabe and Mrs. Jutta Colberg are gratefully acknowledged.

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