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

HRID 15899

反応式

HRID 15899 の反応式
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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24290Palladium Chloride触媒HCID 70681Tetrabutylammonium Chloride触媒HCID 313Hydrochloric Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-c3abfdc781784af8ae3f38b4d5d92de5
出典データセット
uspto-grants-2010_06
特許番号
US07732600B2

関連ノート

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