Diethyl Ether → Estra-1,3,5(10),16-tetraen-3-ol

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Reaction Steps

Estra-1,3,5(10),16-tetraen-3-ol, for example, may be prepared from estrone (estra-1,3,5(10)-trien-3-ol-17-one) by reacting estrone with an appropriate amount of p-toluenesulfonylhydrazide in a polar solvent such as dry methanol or ethanol under reflux to form the corresponding estrone p-toluenesulfonylhydrazone. The estrone p-toluenesulfonylhydrazone is then reacted with n-butyl lithium in an inert aprotic solvent such as dry tetrahydrofuran, ether, dimethoxyethane or the like to give estra-1,3,5(10),16-tetraen-3-ol.

Provenance & Evidence