Acetone → HCID 69363153, compound

Participants

Reaction Steps

While stirring 20 ml of an acetone solution of 2.1 g of 1-(3-benzylphenyl)-2,5-dihydropyrrole on an ice bath, 2.2 ml of a 50% aqueous solution of N-methylmorpholine-N-oxide, 4 ml of water and 0.5 ml of a 2.5% t-butanol solution of osmium tetroxide were successively added thereto, followed by stirring as it was at room temperature overnight. After adding 2 ml of a 1 M aqueous solution of sodium thiosulfate, the reaction mixture was extracted with ethyl acetate-water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography with 10–50% ethyl acetate/hexane, to give 1.15 g of the title compound.

Provenance & Evidence