Реакция #1051054
ord-6f94d5514df347a69043a51205d0161c
Уравнение реакции
Реактанты
Растворители
Условия реакции
Обработка
- 1workup.STIRRINGThe resulting solution was stirred at -78° C. to room temperature for 1 h
- 2workup.STIRRINGThe resulting mixture was stirred at room temperature for 10 min
- 3Температураheated at 50° C. for 1 h
- 4ДругоеThe reaction was quenched by the addition of sat. aqueous NH4Cl
- 5ЭкстракцияThe mixture was extracted with EtOAc (2×)
- 6Промывкаwashed with brine
- 7СушкаThe organic phase was dried over Na2SO4
- 8Концентрированиеconcentrated in vacuo
- 9ДругоеThe 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, 1.6M 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 mL of tetrahydrofuran was added. The resulting solution was stirred at -78° C. to room temperature for 1 h 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.