Reacción #70843

Ecuación de reacción

Water

4-methylpyrimidine

NaH

ethyl 4-fluorobenzoate

→

desired compound

Rendimiento 48.0%

1-(4-Fluorophenyl)-2-pyrimidin-4-ylethanone

Rendimiento 48.0%

Disolventes

hexane EtOAc

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was evaporated
2. 2
   workup.ADDITIONThe residue was taken up in a mixture of EtOAc and brine
3. 3
   OtroThe phases were separated
4. 4
   SecadoThe combined organic phases were dried over Na2SO4
5. 5
   Concentraciónconcentrated to dryness
6. 6
   OtroThe crude product obtained by chromatography on silica gel
7. 7
   Temperaturaof increasing polarity as eluent

Procedimiento

To a suspension of NaH (2.26 g 50%, 47.7 mmol) in DMF (92 mL) under argon atmosphere and cooled to 0° C., 4-methylpyrimidine (3.00 g, 31.9 mmol) was added slowly. Then, ethyl 4-fluorobenzoate (6.40 g, 38.2 mmol) was added and it was stirred at room temperature overnight. Water was added and the solvent was evaporated. The residue was taken up in a mixture of EtOAc and brine. The phases were separated and the aqueous phase was reextracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 3.30 g of the desired compound (yield: 48%).

Fuente