Реакция #44135

Уравнение реакции

N,N′-dimethyl-1,2-ethanediamine

2-(3-bromophenyl)ethanol

N,N′-dimethyl-1,2-ethanediamine

potassium carbonate

ammonium chloride

→

title compound

Выход 64.0%

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

Выход 64.0%

Растворители

dioxane

Условия реакции

Обработка

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

Методика

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).

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