Réaction #62197

Équation de réaction

sodium acetate

ammonium acetate

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

→

title compound

Rendement 41.0%

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

Rendement 41.0%

Solvants

acetic acid

Conditions de réaction

Traitement

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

Mode opératoire

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]+.

Source