Radiolabelling with organomercury compounds. Part 1. The synthesis and structure of 6-halocholest-5-en-3β-ols

Abstract

The synthetic route to 6-chloromercuricholest-5-en-3β-ol has been studied and the yield improved from 2% to 20%. The reaction of 6-chloromercuricholest-5-en-β-ol with fluorine, chlorine, bromine, and iodine has been examined. 6-Bromocholest-5-en-3β-ol and 6-chlorocholest-5-en-3β-ol have been directly prepared from 6-iodocholest-5-en-3β-ol using cuprous halides. A new intermediate, 6-tosyloxycholest-5-en-3β-ol, has also been synthesized by the action of silver tosylate on 6-iodocholest-5-en-3β-ol. The structures of the compounds were proven by a combination of high-resolution 1Hmr and 13Cmr. A new crystal modification of 6-chloromercuricholest-5-en-3β-ol has been found.