반응 #216705

반응 방정식

Diethylazodicarboxylate

4-(2'-hydroxy-ethyl)-5-methyl-2-phenyloxazole

triphenylphosphine

3'-hydroxyacetophenone

HCl

→

solid

수율 77.2%

1-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-ethanone

수율 77.2%

용매

H2O

THF

THF

반응 조건

후처리

1. 1
   기타to come to room temperature
2. 2
   추출extracted with EtOAc
3. 3
   건조The organic extracts were dried over MgSO4
4. 4
   기타Evaporation and purification by flash chromatography on silica gel (hexane/EtOAc 5/1)

실험 절차

Diethylazodicarboxylate (20.7 mL, 131.6 mmol) in THF (35 mL) was added dropwise in to a cold (0° C.) solution of 4-(2'-hydroxy-ethyl)-5-methyl-2-phenyloxazole (25.0 g, 123.0 mmol), triphenylphosphine (34.5 g, 131.6 mmol), and 3'-hydroxyacetophenone (18.0 g, 131.6 mmol) and THF (180 mL). The mixture was allowed to come to room temperature and stirred for 48 hours. Then, it was poured into H2O, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexane/EtOAc 5/1) gave a white solid (30.5 g, 77% yield, m.p. 70°-71° C.). Analysis for: C20H19NO3Calc'd: C, 74.75; H, 5.96; N, 4.36 Found: C, 74.70; }I, 6.15; N, 4.28

출처