Reaktion #44135

Reaktionsgleichung

N,N′-dimethyl-1,2-ethanediamine

2-(3-bromophenyl)ethanol

N,N′-dimethyl-1,2-ethanediamine

potassium carbonate

ammonium chloride

→

title compound

Ausbeute 64.0%

3-[3-(2-Hydroxyethyl)phenyl]-1,3-oxazolidin-2-one

Ausbeute 64.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for another 2 h at 100° C
3. 3
   TemperaturAfter cooling down to room temperature
4. 4
   Extraktionextracted with dichloromethane
5. 5
   TrocknenThe organic layer was dried over magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe crude compound was purified by flash chromatography on silica gel
8. 8
   Wascheneluting with ethyl acetate-cyclohexane (1:1 to 1:0)

Vorschrift

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).

Quelle