Réaction #44177

Équation de réaction

N-(3-iodo-phenyl)-methanesulfonamide

allyl alcohol

sodium hydrogencarbonate

→

title compound

Rendement 60.5%

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

Rendement 60.5%

Solvants

dimethylformamide

hydrochloric acid

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source