
TY  - JOUR
A1  - Collins, DJ 
A1  - Hobbs, JJ 
T1  - The synthesis of <I>meso</I>-Hexoestrol[3,4-D<sub>2</sub>] and some related specifically deuterated compounds
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1974
VL  - 27
IS  - 8
SP  - 1743
EP  - 1751
KW  - 
UR  - https://doi.org/10.1071/CH9741743 
N2  - Condensation of p-methoxyphenylacetonitrile with p-methoxypropiophenone in the presence of sodium hydride in dimethyl sulphoxide at 65º gave (Z)-(23%) and (E)-2,3-bis(p-methoxyphenyl)pent-2-enenitrile(16%). The reduction of this &#945;,&#946;-unsaturated nitrile with lithium aluminium deuteride in tetrahydrofuran, and workup with D2O or with H2O, gave high yields of erythro-2,3-bis(p-methoxy-phenyl)valeronitrile[2,3-D2], or -[3-D], respectively. Conversion of the dideuteronitrile into the corresponding methyl ketone with methylmagnesium iodide, followed by a hydride reduction-tosylation-hydride reduction sequence, then demethylation, afforded meso-hexoestrol[3,4-D2]. Dehydration of (3RS,4SR)-3,4-bis(p-methoxyphenyl)hexan-2&#958;-ol[3,4-D2] with phosphoryl trichloride in pyridine gave 3,4-bis(p-methoxyphenyl)hex-2-ene[4-D]. Reduction of erythro-2,3-bis(p-methoxy- phenyl)valeronitrile[3-D] to the corresponding amine followed by quaternization and Hofmann elimination afforded 2,3-bis(p-methoxypheny1)pent-1-ene[3-D]. 
ER  -

