N,N'-Dimethylethylenediamine → 3-[3-(2-Hydroxyethyl)phenyl]-1,3-oxazolidin-2-one

Temperature

100 °C

A solution 2-(3-bromophenyl)ethanol (1.00 g, 5.00 mmol), 2-oxazolidin-2-one (874 mg, 10.04 mmol), copper(I)iodide (96 mg, 0.50 mmol), N,N′-dimethyl-1,2-ethanediamine (60 μL, 49 mg, 0.56 mmol) and potassium carbonate (1.04 g, 7.50 mmol) were suspended in dioxane (6 mL). The mixture was stirred under nitrogen for 2.5 h at 100° C. After addition of copper(I)iodide (96 mg, 0.50 mmol) and N,N′-dimethyl-1,2-ethanediamine (60 μl, 49 mg, 0.56 mmol) stirring was continued for another 2 h at 100° C. After cooling down to room temperature, the mixture was poured into saturated aqueous ammonium chloride solution and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel, eluting with ethyl acetate-cyclohexane (1:1 to 1:0) affording the title compound in 64% yield (664 mg).

1. stirringstirring
2. waitwas continued for another 2 h at 100° C
3. temperatureAfter cooling down to room temperature
4. extractionextracted with dichloromethane
5. dry with materialThe organic layer was dried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe crude compound was purified by flash chromatography on silica gel
8. washeluting with ethyl acetate-cyclohexane (1:1 to 1:0)

ORD record

ord-46fd82e252454dabba623ce578f3824f

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592346B2