Reaction #62197

Reaction equation

sodium acetate

ammonium acetate

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

→

title compound

Yield 41.0%

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

Yield 41.0%

Solvents

acetic acid

Conditions

Workup

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

Procedure

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