تفاعل #44177

معادلة التفاعل

N-(3-iodo-phenyl)-methanesulfonamide

allyl alcohol

sodium hydrogencarbonate

→

title compound

المردود 60.5%

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

المردود 60.5%

المذيبات

dimethylformamide

hydrochloric acid

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر