Reaktion #44177

Reaktionsgleichung

N-(3-iodo-phenyl)-methanesulfonamide

allyl alcohol

sodium hydrogencarbonate

→

title compound

Ausbeute 60.5%

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

Ausbeute 60.5%

Lösungsmittel

dimethylformamide

hydrochloric acid

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle