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

HRID 584611Notes

Reaction equation

HRID 584611 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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]).

Workup

  1. washwashed
  2. dry with materialDrying over sodium sulfate, evaporation of the solvent and flash chromatography on silica gel

Sources & evidence

ORD record
ord-c3ac794dfa484565a6fbd3b08e28baf9
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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