Tetrahydrofuran → HCID 54006954, compound

Participants

Reaction Steps

20 g. of 6-ethoxycarbonylmethyl-1,3,5(10),6-estratetraene-3,17β-diol is hydrogenated in 280 ml. of tetrahydrofuran and 280 ml. of methanol in the presence of 2 g. of Pd/CaCO3 (10%) until 1 millimole of hydrogen has been absorbed per millimole of substance. The thus-obtained product is 6β-ethoxycarbonylmethyl-1,3,5(10)-estratriene-3,17β-diol as a foamy mass. The same compound is also produced by the analogous hydrogenation of 6-ethoxycarbonylmethylene-1,3,5(10)-estratriene-3,17β-diol. The preparation of 6β-ethoxycarbonylmethyl-1,3,5(10)-estratriene-3,17β-diol can be simplified by hydrolyzing the crude product of the Reformatskii reaction, freeing the thus-obtained hydrolyzate from by-products by fractional filtration over silica gel, and hydrogenating the evolved mixture of 6-ethoxycarbonylmethyl-1,3,-5(10),6-estratetraene-3,17β-diol and 6-ethoxycarbonylmethylene-1,3,5(10)-estratriene-3,17β-diol as indicated above.

Provenance & Evidence