반응 #44177

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N-(3-iodo-phenyl)-methanesulfonamide

allyl alcohol

sodium hydrogencarbonate

→

title compound

수율 60.5%

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

수율 60.5%

용매

dimethylformamide

hydrochloric acid

반응 조건

후처리

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

실험 절차

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%).

출처