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

HRID 965892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965892
[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]

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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]).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6a32b50ab1a548b99d3dabbb20199387
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951874B2

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