反応 #471293

反応方程式

citric acid

ethyl 2,3-dibromo-3-(5-((2-phenoxybenzyl)oxy)-2-pyridinyl)propanoate

hydroxyamine hydrochloride

sodium hydroxide methanol

→

title compound

5-(5-((2-phenoxybenzyl)oxy)pyridin-2-yl)isoxazol-3-ol

溶媒

water

tetrahydrofuran

water

反応条件

後処理

1. 1
   温度heated
2. 2
   温度to reflux overnight
3. 3
   温度The reaction solution was cooled
4. 4
   抽出extracted with chloroform
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   その他the residue obtained
8. 8
   その他was purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid)
9. 9
   workup.DISTILLATIONThe solvent of the resultant fraction was distilled off under reduced pressure
10. 10
    その他purification by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., chloroform/methanol (9:1))

実験手順

To a solution of ethyl 2,3-dibromo-3-(5-((2-phenoxybenzyl)oxy)-2-pyridinyl)propanoate (159.3 mg) in tetrahydrofuran (1 ml), 32 mg of hydroxyamine hydrochloride, 0.6 ml of 2.5N sodium hydroxide/methanol solution and 0.078 ml of water were added, and the reaction solution was stirred at room temperature for 2 hours and then heated to reflux overnight. The reaction solution was cooled, then diluted with water, acidified with 10% aqueous citric acid, then extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid). The solvent of the resultant fraction was distilled off under reduced pressure, and then purification by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., chloroform/methanol (9:1)) was carried out to afford the title compound as a white solid.

出典