Tributylstannane → 2-Cyclopenten-1-one, 3-(tributylstannyl)-

참여 물질

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반응 단계

3-Ethoxy-cyclopent-2-enone (1.0 g, 7.9 mmol) was dissolved in THF (2 ml) and was placed in an addition funnel atop a flask equipped with stirring and a cooling bath. The flask was charged with THF (10 ml) and diisopropylamine (0.88 g, 8.7 mmol) and cooled to 0° C. To the solution was added n-butyllithium (1.9M, 4.6 ml) and the resulting solution stirred for five minutes. While still at 0° C., tributyltinhydride (2.35 ml, 8.7 mmol) was added to give a yellow solution, then after 15 minutes at 0° C., the solution was cooled to -70° C. At -70° C. the 3-ethoxy-cyclopent-2-enone was added dropwise, and after addition was complete, the reaction was stirred at -20° for one hour. The cooling bath was removed and the reaction quenched with NH4Cl solution and diluted with ether. The organic layer was separated, dried (MgSO4), filtered, and evaporated to give an oil. Chromatography on silica gel with CH2Cl2 gave the title compound (1.8 g).

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