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Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator

Donna D Yu1, Barry M Forman

  • 1Division of Molecular Medicine, The Beckman Research Institute, The City of Hope National Medical Center, Duarte, California 91010, USA.

The Journal of Organic Chemistry
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Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major product and...