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An Environmentally Friendly Process for the Preparation of 16‐Dehydropregnenolone Acetate
Author(s) -
Yan Zhang,
YongYong Liu,
XueXin Cheng,
XueSong Wang,
BaoWen Zhang
Publication year - 2005
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200590753
Subject(s) - environmentally friendly , chemistry , oxidizing agent , acetone , acetic anhydride , yield (engineering) , singlet oxygen , organic chemistry , solvent , pyridine , green chemistry , combinatorial chemistry , oxygen , catalysis , reaction mechanism , ecology , materials science , metallurgy , biology
Instead of environmentally toxic chromium oxidant, singlet oxygen generated photochemically was used as environmentally friendly and benign oxidizing agent to accomplish the transformation of pseudodiosgenin diacetate to diosone efficiently in a low toxic and less expensive solvent acetone. Accordingly 16‐dehydropregnenolone acetate (16‐DPA), an important intermediate for preparation of steroidal drugs, was prepared in good yield (75%) when photoreaction was run in acetone/acetic anhydride/pyridine system. The mild reaction condition as well as simple and environmentally friendly process made the method commercially viable and important for production of 16‐DPA in industrial scale.