Potassium Hydroxide → HCID 58453198, compound

Participants

Reaction Steps

The 1-cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate is dissolved in 15 ml of dimethyl sulfoxide and 0.17 g of potassium hydroxide (2.48 mmol) is added, and stirring is carried out for 5 hours at ambient temperature. The reaction mixture is added to ice-water. Extraction is carried out with ethyl acetate and the organic phase is dried over sodium sulfate and concentrated by evaporation. Chromatography on silica gel is carried out in order to remove by-products (eluant: ethyl acetate/hexane 1:15). After removal of the eluant, 0.28 g of 2-(2-nitrophenyl)-bicyclopropane (61% of theory) is obtained in the form of a brownish liquid (trans:cis ratio: 4.5:1). 1H-NMR of trans-2-(2-nitrophenyl)-bicyclopropane (CDCl3-ppm): 0.17/m/1H, 0.19/m/1H, 0.42/m/1H, 0.48/m/1H, 0.83/m/1H, 0.84/m/1H, 0.99/m/1H, 1.13/m/1H, 2.17/m/1H, 7.10/dd/1H, 7.25/m/1H, 7.45/m/1H, 7.78/dd/1H); 1H-NMR of cis-2-(2-nitrophenyl)-bicyclopropane (CDCl3-ppm): −0.09/m/1H, 0.02/m/1H, 0.06/m/1H, 0.27/m/1H, 0.71/m/1H, 0.85/m/1H, 0.98/m/1H, 1.10/m/1H, 2.53/m/1H, 7.35/m/1H, 7.45/m/1H, 7.52/m/1H, 7.92/dd/1H.

Provenance & Evidence