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The synthesis of trideuterated diethylstilbestrol ([1,1,1-D3] E-3,4-di-(4-hydroxyphenyl)-hex-3-ene)

โœ Scribed by Penelope J. Marshall; Lewis L. Engel

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

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โœฆ Synopsis

I, I, l-D31 ~-3,4-Di-fI-hydroxyphenyI)-her3-ene has been synthesized from I, 2-di-f4-rnethoxyphenyI)-butan-l-one.

Reaction of t h i s ketone w i t h [2,2,2-D3] e t h y l magnesium iodide y i e l d s [ l , l , l-D3]3,4-di-f4-methoxyphenyl)-hexan-3-ol, which on dehydration w i t h potassium hydrogen s u l f a t e a d demethykztion w i t h methyl magnesim iodide y i e l d s i s o t o p i c a l l y pure trideuterated d i e t h y ls t i t b e s t r o t . hex-3-ene cannot be prepared by t h i s route porn [1,1-D21 ethgl magnesium i o d i d e . I s o t o p i c a l l y pure [ 2, 2-D2] 3,4-di-f4-dydroxyphengt)-

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Synthesis of hexadeuterated diethylstilb
Synthesis of hexadeuterated diethylstilbestrol ([1,1,1,6,6,6-d6]-E-3,4-di-(4-hydroxyphenyl)-hex-3-ene)
โœ Gijsbert Zomer; Henk J. G. M. Derks; Hans Wynberg ๐Ÿ“‚ Article ๐Ÿ“… 1983 ๐Ÿ› John Wiley and Sons ๐ŸŒ French โš– 184 KB ๐Ÿ‘ 1 views

d61-E-3,4-di-(4-hydroxyphenyl)-hex-3-ene was s y nt h e s i z e d from [1,?,1-d31-4-methoxypropiophenone by r e d u c t i v e coup l i n g . The p r e p a r a t i o n o f [1,1,1-d31-4-methoxypropiophenone i nv o l v e d r e a c t i o n o f p -a n i s o y l c h l o r i d e w i t h p e r d e u t e r a

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