反応 #44177

反応方程式

N-(3-iodo-phenyl)-methanesulfonamide

allyl alcohol

sodium hydrogencarbonate

→

title compound

収率 60.5%

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

収率 60.5%

溶媒

dimethylformamide

hydrochloric acid

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate (2×100 mL)
2. 2
   乾燥The combined organic layers were dried (sodium sulfate)
3. 3
   その他evaporated in vacuo
4. 4
   その他The crude product was purified by silica gel chromatography (ethyl acetate in hexane, 30% to 50%)

実験手順

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%).

出典