Explain the step in the synthesis of tamoxifen ?

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Explain the step in the synthesis of tamoxifen ?

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Step 1

There are two general methods for preparation of tamoxifen. First double bonds are formed through tertiary alcohol and secondly by reductive coupling of aromatic ketone which occur in the presence of transition metal as catalyst.

Friedel Crafts alkylation reaction is used for synthesis of acid catalyzed. 

Substrate like benzaldehyde and cinnamyltrimethylsilane undergoes three component coupling reaction. The reaction includes Cl2Hf(OTf)2 or Hf(OTf)4 and co-catalyst TmSCl are used. 

Bulky catalyst like tertiary butoxide is preferred for production of tetra substituted alkene. The reaction mechanism can be shown as

 

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