Реакция #722770
ord-0cc0c3fdbaef4c149c2404c1a237f58e
Уравнение реакции
Реактанты
Растворители
Условия реакции
Обработка
- 1workup.STIRRINGThe resulting mixture was stirred at room temperature for 10 min
- 2Температураheated at 50° C. for 1 h
- 3ДругоеThe reaction was quenched by the addition of sat. aqueous NH4Cl
- 4ЭкстракцияThe mixture was extracted with EtOAc (2×)
- 5Промывкаwashed with brine
- 6СушкаThe organic phase was dried over Na2SO4
- 7Концентрированиеconcentrated in vacuo
- 8ДругоеThe crude material product was purified by flash chromatography (silica, 15% ethyl acetate in hexanes)
Методика
A solution of lithiothiophene was prepared by the addition of 0.10 g (0.095 mL, 1.2 mmol) of thiophene to a cold solution (−78° C.) of 0.61 g (0.90 mL, 1.4 mmol, 1.6 M in hexanes) of n-butyl lithium in 2.0 mL of tetrahydrofuran. The solution was stirred at −78° C. for 35 min and then a solution of 0.158 g (1.2 mmol) of zinc chloride in 2.0 mnL of tetrahydrofuran was added. The resulting solution was stirred at −78° C. to room temperature for 1h and then the organozinc was added via cannula to a mixture of 0.212 g (0.44 mmol) of ethyl (E)-4-[2-(5,5-dimethyl-8-(trifluoromethylsulfonyl)oxy-5,6-dihydronaphthalen-2-yl)ethenyl] benzoate (Compound A9) and 18 mg (0.016 mmol) of tetrakis(triphenylphosphine)palladium(0) in 2.0 mL of tetrahydrofuran. The resulting mixture was stirred at room temperature for 10 min and then heated at 50° C. for 1 h. The reaction was quenched by the addition of sat. aqueous NH4Cl. The mixture was extracted with EtOAc (2×), and washed with brine. The organic phase was dried over Na2SO4 and then concentrated in vacuo. The crude material product was purified by flash chromatography (silica, 15% ethyl acetate in hexanes) to afford the title compound as a solid.