Dichloromethane → N-[2-(7-oxabicyclo[4.1.0]hept-2-yloxy)phenyl]acetamide

HRID 965892노트

반응식

HRID 965892 반응식
[CH:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15](=[O:17])[CH3:16])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.ClCCl.C(OCC)(=[O:23])C>>[CH:2]12[O:23][CH:3]1[CH2:4][CH2:5][CH2:6][CH:1]2[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:17])[CH3:16]

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 22313659N-[2-(2-cyclohexen-1-yloxy)phenyl]acetamide

생성물 1

HCID 22313696N-[2-(7-oxabicyclo[4.1.0]hept-2-yloxy)phenyl]acetamide수율 73%

실험 절차

To a solution of N-[2-(2-cyclohexen-1-yloxy)phenyl]acetamide (76 mg, 329 μmol, 1.0 equiv.) in dichloromethane (5 ml) m-chlorobenzoic acid (85 proz.; 121 mg, 559 μmol, 1.7 equiv.) was added at 0° C. Stirring was continued overnight while the reaction mixture was allowed to warm up slowly to room temperature. The heterogenous mixture was diluted with ethyl acetate and washed with sat. sodium sulfite, 5% sodium hydroxide and brine. Drying over sodium sulfate, evaporation of the solvent and flash chromatography on silica gel provided 59 mg (73%) of the title compound as a mixture of the diastereoisomers (ratio A:B=trans:cis=5:3 [1H-NMR]).

후처리

  1. washwashed with sat. sodium sulfite, 5% sodium hydroxide and brine
  2. dry with materialDrying over sodium sulfate, evaporation of the solvent and flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-6a32b50ab1a548b99d3dabbb20199387
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951874B2

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