Реакция #44177

Уравнение реакции

N-(3-iodo-phenyl)-methanesulfonamide

allyl alcohol

sodium hydrogencarbonate

→

title compound

Выход 60.5%

N-[3-(3-Oxo-propyl)-phenyl]-methanesulfonamide

Выход 60.5%

Растворители

dimethylformamide

hydrochloric acid

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate (2×100 mL)
2. 2
   СушкаThe combined organic layers were dried (sodium sulfate)
3. 3
   Другоеevaporated in vacuo
4. 4
   ДругоеThe crude product was purified by silica gel chromatography (ethyl acetate in hexane, 30% to 50%)

Методика

A mixture of N-(3-iodo-phenyl)-methanesulfonamide (2.4 g, 8 mmol), tetra-n-butyl-ammonium chloride (2.22 g, 8 mmol), allyl alcohol (0.7 g, 12 mmol), sodium hydrogencarbonate (1.6 g, 19 mmol) and palladium(II) chloride (0.36 g, 1.8 mmol) in anhydrous dimethylformamide (30 mL) was stirred at room temperature for 48 h under argon. The mixture was then diluted with 5% aqueous hydrochloric acid (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were dried (sodium sulfate) and evaporated in vacuo. The crude product was purified by silica gel chromatography (ethyl acetate in hexane, 30% to 50%) to give the title compound as an amber oil (1.1 g, 60%).

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