Реакция #52338

Уравнение реакции

ethyl-2-fluoro-4-trifluoromethylsulfonyloxy-benzoate

Intermediate 6

ethyl-2-fluoro-4-trifluoromethylsulfonyloxy-benzoate

(trimethylsilyl)acetylene

→

title compound

Выход 94.6%

Ethyl-2-fluoro-4-trimethylsilanylethynyl-benzoate

Выход 94.6%

Растворители

diethyl ether

triethyl amine

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеsparged with argon
2. 2
   Другоеthe resulting reaction mixture
3. 3
   ТемператураIt was then cooled to ambient temperature
4. 4
   Фильтрацияfiltered over a bed of celite
5. 5
   ДругоеThe filtrate was evaporated in vacuo to an oil which

Методика

A solution of ethyl-2-fluoro-4-trifluoromethylsulfonyloxy-benzoate (Intermediate 6, 1.82 g, 6 mmol) in triethyl amine (12 mL) and anhydrous tetrahydrofuran (30 mL) was treated with copper(I)iodide (0.12 g, 0.6 mmol) and sparged with argon. Dichlorobis(triphenylphosphine)palladium(II) (0.43 g, 0.6 mmol) was added followed by (trimethylsilyl)acetylene (3.6 mL, 24 mmol) and the resulting reaction mixture was heated at 70° C. overnight. It was then cooled to ambient temperature, diluted with diethyl ether and filtered over a bed of celite. The filtrate was evaporated in vacuo to an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent to afford the title compound as an orange oil (1.5 g, quantitative).

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