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No.87 (2009/3) >

 
Title :Preparation of (Z)-3-acetoxy-5-carbomethoxy-l-cyclohexene
Authors :Suzuka, Toshimasa
Nagatomi, Yurie
Authors alternative :鈴鹿, 俊雅
Issue Date :Mar-2009
Abstract :(Z)-3-Acetoxy-5-carbomethoxy-l-cyclohexene was prepared via according to the reported procedures. Thus, iodolactonization of (rac)-3-cyclohexene-l-carboxylic acid followed by elimination of iodide with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave the unsaturated lactone in 86% yield for 2 steps. Alcoholysis of the obtained lactone with sodium methoxide in methanol afforded (Z)-5-carbomethoxy-3-hydroxy-1-cyclohexene in 95% yield with sole isomer. Acetylation of the alcohol 4 was carried out with AcCl and pyridine in CH_2CI_2 at 0 ℃ for 40 min to give (Z)-3-acetoxyl-5-carbomethoxy-l-cyclohexene in 22% yield with a mixture of 88% Z-isomer and 12% E-isomer.
Type Local :紀要論文
ISSN :0286-9640
Publisher :琉球大学理学部
URI :http://hdl.handle.net/20.500.12000/9535
Citation :琉球大学理学部紀要 = Bulletin of the College of Science. University of the Ryukyus no.87 p.77 -79
Appears in Collections:No.87 (2009/3)

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