4-Phenyl-3-trimethylsilylpyrazole (10). A solution of 9 prepared from TMSCHN2 and BuLi was treated with cinnamonitrile 8 (129 mg, 1 mmol) in THF (2 mL). After 0.5 h stirring at -78 ℃ and 1.5 h at -45 ℃, the reaction mixture was quenched with aq NH4Cl. Usual workup and chromatography (silica gel, CHCl3:Et2O, 20:1) gave 190 mg of 10 (88%), mp 117–118.5 ℃. 【Heterocycles, 1988, 27, 343】 1 Pechman von H Chem Ber 1898 31 2950 2 Sheenan JC J Am Chem Soc 1949 71 4059 3 Matteson DS J Org Chem 1962 27 4293 4 Huisgen R Angew Chem 1963 75 604 5 Shioiri T Tet Lett 1984 25 433 6 Aoyama T Heterocycles 1988 27 343 7 Sandhu JS ARKIVOC 2007 xv 18 参考资料 一、Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 367. 二、Comprehensive Organic Name Reactions and Reagents, by Zerong Wang,2147-2150. |
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