Allyl Alcohol → N-[3-(3-Oxo-propyl)-phenyl]-methanesulfonamide

HRID 15899

반응식

HRID 15899 반응식
I[C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:13]([OH:16])[CH:14]=[CH2:15].C(=O)([O-])O.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.Cl.[Pd](Cl)Cl>[O:16]=[CH:13][CH2:14][CH2:15][C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 3

HCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 21830928N-(3-iodophenyl)methanesulfonamide

생성물 1

HCID 57444373N-[3-(3-Oxo-propyl)-phenyl]-methanesulfonamide수율 60.5%

시약·촉매·용매 4

HCID 24290Palladium Chloride촉매HCID 70681Tetrabutylammonium Chloride촉매HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매

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%).

후처리

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

출처 및 근거

ORD 기록
ord-c3abfdc781784af8ae3f38b4d5d92de5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732600B2

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