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KMID : 1059519960400040243
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Journal of the Korean Chemical Society
1996 Volume.40 No. 4 p.243 ~ p.248
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A Newer Short Synthesis of dl-Muscone(Ⅰ)
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Im D,-S.
Shin Dae-Hee
Park Dai-Kyu
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Abstract
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New routes have been developed for the practical syntheses of dl-Muscone(1) employing cyclopentadecanone(2) as the starting material. In this experiment, addition of bromine to cyclopentadecanone in dried E. Ether solution with a trace of AlCl3 as the catalyst were produced 2-bromocyclopentadecanone(3). This process was enhanced formation of regioselective enolate anion at C2 position. 2-Bromocyclopentadecanone was put into Li2CO3-LiBr-DMF solution at 140∼150℃, were produced trans- and cis-2-cyclopentadecen-1-one(4) mixture. Other by-products were reduced by control of reaction temperature and time. Trans- and cis-2-cyclopentadecen-1-one(4) mixture was directly put into dried E. Ether solvent and induce to react dropwise with CH3MgBr-Cu2Cl2 complex, all of them got into 1,4-addition, dl-Muscone (1) was formed as the result. Conculsion, through three steps procedure from cyclopentadecanone(2) to dl-Muscone(1), the pure dl-Muscone was obtained with the high proportion of 85%, and synthetic cost was able to be much lower than any other conventional methods as there were no chemical separating steps.
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