Synthesis of 4-Methyl-4-aza-21E-benzylidene-5-pregnene-3,20-dione

doi:10.11944/j.issn.1000-0518.2017.06.160354

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (6): 671-675.DOI: 10.11944/j.issn.1000-0518.2017.06.160354

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Synthesis of 4-Methyl-4-aza-21E-benzylidene-5-pregnene-3,20-dione

CHEN Shaorui(),SHEN Fengjuan

College of Science,Hebei University of Science and Technology,Shijiazhuang 050018,China

Received:2016-09-05 Accepted:2016-12-28 Published:2017-05-31 Online:2017-05-31
Contact: CHEN Shaorui
Supported by:
Supported by Natural Science Foundation of Hebei Province(No.B2012208036), the Project of Opening Laboratory of Hebei University of Science and Technology

Abstract

Abstract:

The method of synthesis of 4-methyl-4-aza-21E-benzylidene-5-pregnene-3,20-dione catalyzed by KF/Al₂O₃ was reported. 4-Methyl-4-aza-5-pregnene-3,20-dione, as a key intermediate, was synthesized by cleavage of A-ring and ring-closure from progesterone and which was then converted to the target product through Claisen condensation catalyzed by KF/Al₂O₃. The effects of different catalysts, reaction temperature and catalyst dosage were investigated. 56%~68% yields are obtained under optimal conditions:n(3)∶n(KF/Al₂O₃)=1∶1, reaction time 4 h under reflux. This study provides a simple and efficient approach to the synthesis of 4-aza-steroidal benzylidene derivatives.

Key words: potassium fluoride/aluminum oxide, condensation reaction, benzylidene steroidal derivatives

CHEN Shaorui, SHEN Fengjuan. Synthesis of 4-Methyl-4-aza-21E-benzylidene-5-pregnene-3,20-dione[J]. Chinese Journal of Applied Chemistry, 2017, 34(6): 671-675.

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Synthesis of 4-Methyl-4-aza-21E-benzylidene-5-pregnene-3,20-dione

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