Dimethyl Sulfoxide → HCID 14798965, compound

Participants

Reaction Conditions

Reaction Steps

130 ml of abs. DMSO are slowly added dropwise at 10° C. to 6.6 g (0.22 mol) of sodium hydride (80% in oil) and 34.2 g (0.16 mol) of trimethylsulphoxonium iodide. The mixture is stirred for one hour at 20° C. and then 26.3 g (0.14 mol) of 1-cyanocyclopropyl-4-fluorophenyl ketone (compound II-2, Example 19, dissolved in 65 ml of abs. DMSO) are added dropwise. The mixture is stirred for 14 h at 20° C. The solution is poured into water and the mixture is extracted with ethyl acetate. The combined organic phases are washed with H2O and dried over Na2SO4, and the solvent is evaporated in vacuo. The residue is chromatographed on silica gel and 15 g (54% of theory) of 2-(1-cyanocyclopropyl)-2-(4-fluorophenyl)oxirane are obtained in the form of a colorless oil after evaporating the solvent, 1H--NMR (CDCl3):

Provenance & Evidence