反応 #44135

反応方程式

N,N′-dimethyl-1,2-ethanediamine

2-(3-bromophenyl)ethanol

N,N′-dimethyl-1,2-ethanediamine

potassium carbonate

ammonium chloride

→

title compound

収率 64.0%

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

収率 64.0%

溶媒

dioxane

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for another 2 h at 100° C
3. 3
   温度After cooling down to room temperature
4. 4
   抽出extracted with dichloromethane
5. 5
   乾燥The organic layer was dried over magnesium sulfate
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The crude compound was purified by flash chromatography on silica gel
8. 8
   洗浄eluting with ethyl acetate-cyclohexane (1:1 to 1:0)

実験手順

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).

出典