
%0 Journal Article
%A Pert, DJ 
%A Ridley, DD 
%T Formylation of Estrogens
%J Australian Journal of Chemistry
%D 1989/03/01
%V 42
%N 3
%P 405-419
%K 
%R https://doi.org/10.1071/CH9890405
%U https://www.publish.csiro.au/paper/CH9890405 
%X Reimer-Tiemann formylations of oestradiol and oestrone were investigated and, whilst substitution was effected under certain conditions to give mixtures of 2- and 4-formyloestrogens, yields were very low and the method was unsuitable for preparative purposes. Regioselective methods were developed and 2-formyloestradiol was conveniently prepared from oestradiol by formylation of the lithio derivative of the bis(methoxymethyl) ether and removal of the rotecting groups with hydrochloric acid. 4-Formyloestradiol was prepared by a sequence of reactions starting with the methoxyethyl ether of 4-bromooestradiol, then metal-halogen interconversion, formylation with N-methylformanilide, and removal of the protecting group. A number of related derivatives, including 2-formyloestriol, were prepared. 
