반응 #1126405

반응 방정식

triethylamine

1,4-phenylenediisocyanate

1-ethynyl-2-methoxy-benzene

5-nitro-pentanoic acid methyl ester

→

yellow oil

수율 112.6%

4-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acid methyl ester

수율 112.6%

용매

toluene

반응 조건

후처리

1. 1
   온도to reflux under N2 overnight
2. 2
   여과Filter mixture through a pad of Celite®
3. 3
   세척rinse with toluene
4. 4
   농축Concentrate

실험 절차

Add 1,4-phenylenediisocyanate (19.22 g, 120.0 mmol) to a stirred solution of 1-ethynyl-2-methoxy-benzene (2204901, 5.29 g, 40.0 mmol) and 5-nitro-pentanoic acid methyl ester (7.91 g, 49.1 mmol) in toluene (300 mL, anhydrous) and stir under N2. Add triethylamine (16.7 mL, 120.0 mmol) and heat to reflux under N2 overnight. Filter mixture through a pad of Celite® and rinse with toluene. Concentrate to get 12.4 g yellow oil. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes to afford the title compound (14.0 g, 74%). MS (IS) 276 (M+1)+.

출처