Reaktion #216705

Reaktionsgleichung

Diethylazodicarboxylate

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

triphenylphosphine

3'-hydroxyacetophenone

HCl

→

solid

Ausbeute 77.2%

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

Ausbeute 77.2%

Lösungsmittel

H2O

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto come to room temperature
2. 2
   Extraktionextracted with EtOAc
3. 3
   TrocknenThe organic extracts were dried over MgSO4
4. 4
   SonstigeEvaporation and purification by flash chromatography on silica gel (hexane/EtOAc 5/1)

Vorschrift

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

Quelle