Chlorination of 3beta-hydroxyl-5-Delta steroids with anhydrous ferric chloride.
Treatment of 3beta-hydroxyl-5-Delta steroids with anhydrous FeCl(3) in CH(2)Cl(2) afforded reasonable yields of the corresponding alkyl chlorides with a retention of configurations. The structures of the chlorine-exchanging products were determined by NMR and HRMS spectra. The absolute configurations were confirmed by X-ray crystal analysis of 3beta-chloro-androst-5-en-17-one. The generality and scope of the reaction were also investigated.
Liu
Feng-Wu
FW
Department of Chemistry, Zhengzhou University, 75 Da Xue Bei Lu, Zhengzhou 450052, PR China.
Liu
Hong-Min
HM
Zhang
Yan-Bing
YB
Zhang
Jing-Yu
JY
Tian
Li-Huan
LH
D002712:Chlorides; D005290:Ferric Compounds / Q000737:chemistry*; D006914:Hydroxysteroids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure
D002712:Chlorides; D005290:Ferric Compounds; D006914:Hydroxysteroids; C024555:ferric chloride