Methyl iodide → HCID 67715428, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4(S)-(1(S)-(3,4-dichlorophenyl)-3-butenyl)-2-oxazolidinone (3.25 g, 11.4 mmol) in DMF (25 mL) at room temp was added NaH (573 mg, 95%, 22.7 mmol). The mixture was stirred for 20 min whereupon MeI (3.54 mL, 57.0 mmol) freshly filtered through basic alumina was added and the resultant reaction mixture was stirred at 70° C. for 14 h. The cooled reaction mixture was diluted with H2O (250 mL) and extracted with EtOAc (3×125 mL). The combined organic extracts were washed with H2O (3×100 mL), brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel 60, 1-5% MeOH/CH2Cl2) to afford the title compound (2.93 g, 86%) as a colorless solid and recovered starting material (382 mg, 11%).

Provenance & Evidence