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

HRID 496190ノート

反応式

HRID 496190 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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]).

後処理

  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

出典と根拠

ORDレコード
ord-84bf286c424f4c6bb6ebb0523246663b
出典データセット
uspto-grants-2005_09
特許番号
US06943188B2

反応ノート

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