Facile route to ferrocifen, 1-[4-(2-dimethylaminoethoxy)]-1-(phenyl-2-ferrocenyl-but-1-ene), first organometallic analogue of tamoxifen, by the McMurry reaction

As part of the search for tamoxifen substitutes that could be useful in the treatment of breast cancer, the use of organometallic complexes has been investigated. For this purpose a synthesis has been developed for ferrocifen, the prototype of this new series of complexes. Low valent titanium-mediated (TiCl4/Zn) cross-coupling of 4-MeO-C6H4COPh with ferrocenyl ethyl ketone affords the corresponding but-l-ene in high yield (66%), from which ferrocifen, 3, is rapidly prepared in an overall yield of 41%.