m-Chloroperbenzoic acid → (+/-)-2-(Benzyloxymethyl)-3-(2-chlorophenyl)oxirane

Participants

Reaction Steps

To a solution of (E)-1-(3-(benzyloxy)prop-1-enyl)-2-chlorobenzene(Preparation example 367, 4.94 g, 22 mmole) in CH2Cl2 (110 mL) was added 3-chloroperoxybenzoic acid (70˜75%, 8 g, 33 mmole) portionwise at 0° C. The mixture was stirred for 18 hr at room temperature. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O at 0° C. then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with sat′ NaHCO3, H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (4.3 g, 60˜80%).

Provenance & Evidence