Reaktion #62197

Reaktionsgleichung

sodium acetate

ammonium acetate

1-(4-(benzyloxy)phenyl)-2-bromo-2-(pyridin-4-yl)ethanone

→

title compound

Ausbeute 41.0%

4-(4-(4-(benzyloxy)phenyl)-2-methyloxazol-5-yl)pyridine

Ausbeute 41.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was then refluxed for 48 h
2. 2
   SonstigeAfter removal of the solvent under vacuum
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   Waschenthe solution was washed with satd NaHCO3
5. 5
   SonstigeThe organic phase was dried
6. 6
   Einengenconcentrated in vacuum
7. 7
   Sonstigeto give an oil, which
8. 8
   Sonstigewas purified via silica gel chromatography (1:3 EtOAc/n-hexane)

Vorschrift

To a mixture of sodium acetate (323 mg, 2.38 mmol) and ammonium acetate (304 mg, 3.95 mmol) in acetic acid (10 mL) was added 1-(4-(benzyloxy)phenyl)-2-bromo-2-(pyridin-4-yl)ethanone (302 mg, 0.79 mmol). The resulting mixture was then refluxed for 48 h. After removal of the solvent under vacuum, the residue was dissolved in ethyl acetate and the solution was washed with satd NaHCO3. The organic phase was dried and concentrated in vacuum to give an oil, which was purified via silica gel chromatography (1:3 EtOAc/n-hexane) to provide 111 mg (41%) of the title compound. 1H NMR (400 MHz, CDCl3) δ: 2.58 (s, 3H), 5.15 (s, 2H), 7.01 (d, 2H), 7.39 (m, 7H), 7.56 (d, 2H), 8.57 (d, 2H). MS m/z: 343 [M+1]+.

Quelle