Dichloromethane → N-{2-(6-oxabicyclo[3.1.0]hex-2-yloxy)phenyl}acetamide

Participants

Reaction Steps

To an ice bath cooled solution of N-[2-(2-cyclopenten-1-yloxy)phenyl]acetamide (149 mg, 686 μmol, 1.0 equiv.) in dichloromethane (4 ml) m-chloroperbenzoic acid (85 proc.; 146 μmol, 1.1 equiv.) was added. After stirring overnight with slowly warming up to an ambient temperature the reaction mixture was diluted by tertbutyl(methyl)ether, washed successively by a sat. sodium bisulfate solution, 5 proc. sodium hydroxide and brine and dried over sodium sulfate. Evaporation of the solvent and flash chromatography on silica gel (ethyl acetate/heptane, 2:3 continued to ethyl acetate) yielded 93 mg (58%) of the subtitle compound as a mixture of the trans, (minor) and the cis (major) diastereoisomeric epoxides as a pale yellow oil. The cis/trans ratio was determined as 2:1 by 1H-NMR.

Provenance & Evidence