반응 #1126390

반응 방정식

triethylamine

1,4-phenylenediisocyanate

1-ethynyl-2-methoxy-benzene

6-nitro-hexanoic acid ethyl ester

→

orange oil

수율 97.9%

5-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester

수율 97.9%

용매

toluene

반응 조건

후처리

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

실험 절차

Add 1,4-phenylenediisocyanate (14.5 g, 90.8 mmol) to a stirred solution of 1-ethynyl-2-methoxy-benzene (4.0 g, 30.3 mmol) and 6-nitro-hexanoic acid ethyl ester (8.6 g, 45.4 mmol) in toluene (300 mL, anhydrous) and stir under N2. Add triethylamine (12.7 mL, 90.8 mmol) and heat to reflux under N2. After 2.5 hours, filter mixture through a pad of Celite® and rinse with toluene. Concentrate to get 9 grams of a orange oil. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes to afford the title compound (14.0 g, 74%).

출처