Indirect electrooxidation of 11α-hydroxy-16,17α-epoxy-progestron

Abstract

Experimental results are described for the mediated electrooxidn. of 11a-hydroxy-16,17a-epoxyprogesterone to form 11-keto-16,17a-epoxyprogesterone. The organic substrate is chem. oxidized by Cr(VI) in a CH2Cl2/H2O (4 mol/L H2SO4) system at 24-26? the presence of a phase transfer agent (Bu4NHSO4) greatly accelerates the reaction. Spent solns. of Cr can be regenerated at a Pt anode in 4 mol/L H2SO4 media with Ag+ as a catalyst. The current efficiency was >70%, and the chem. yield was >95%. The mediated system may be recycled. A probable mechanism for this reaction is suggested.

Key words: REACTION MECHANISM, OXIDATION, MEDIA, CHROMIUM OXIDE, PHASE TRANSFER CATALYSIS, ELECTROLYSIS, EPOXIDE, PROGESTRONE

CLC Number:

O651

Cite this article

CHEN QIRUI;PANG KAI. Indirect electrooxidation of 11α-hydroxy-16,17α-epoxy-progestron[J]. Chin. J. Org. Chem., 1990, 10(2): 129-134.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[2]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[3]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[4]	Xiaoyu Zhang, Xinyan Li, Bing Cui, Zhihui Shao, Mingqin Zhao. Design, Synthesis and Antioxidant Activity of Tetrahydro-β-carbolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2885-2894.
[5]	Yunzhe Zhong, Ying hen, Lei Yu, Hongwei Zhou. Electrochemical Mediated Esterification Reaction of Carboxylic Acids and Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2855-2863.
[6]	Yanhua Gao, Yinpan Zhang, Yan Zhang, Tao Song, Yong Yang. Visible-Light-Induced Aerobic Oxidation of Alcohols over Surface Oxygen Vacancies-Enriched Nb₂O₅ [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2572-2579.
[7]	Yu Tian, Juan Zhang, Wenchao Gao, Honghong Chang. Application of Dimethyl Sulfoxide as Methylating Reagent in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2391-2406.
[8]	Zhijun Ren, Weiwei Luo, Jun Zhou. Recent Progress in Silver-Mediated Tandem Cyclization of N-Arylacrylamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2026-2039.
[9]	Xiantao Ma, Xiaoyu Yan, Yingying Zhu, Shuanglin Niu, Yuxuan Wang, Chao Yuan. Water-Promoted Green Synthesis of Heteroaryl Thioether [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2136-2142.
[10]	Ke Jing, Panke Zhang, Senmiao Xu. Application of 1,4-Azaborines in Organic and Transition Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1742-1750.
[11]	Cunjing Miao, Jiaqi Yao. Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1341-1364.
[12]	Xuzheng Zhang, Fengli Yu, Bing Yuan, Congxia Xie, Shitao Yu. Phase Transfer Catalytic Oxidation of Cyclopentene to Glutaraldehyde by Vanadium Molybdenum Heteropolyacid Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1444-1451.
[13]	Siqiang Fang, Zanjiao Liu, Tianli Wang. Recent Advances of the Atherton-Todd Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1069-1083.
[14]	Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.
[15]	Yueling Liu, Xinxin Zhong, Ganbing Zhang. Density Functional Theory Study for Exploring the Mechanisms of the [3＋2] Cycloaddition Reactions between 1-R-3-Phenylpropylidenecyclopropane (R=Me/H) and Furfural Catalyzed by Pd(0) [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 660-667.

11α-羟基-17, 17α-环氧黄体酮的间接电解氧化