Reaktion #70843

Reaktionsgleichung

Water

4-methylpyrimidine

NaH

ethyl 4-fluorobenzoate

→

desired compound

Ausbeute 48.0%

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

Ausbeute 48.0%

Lösungsmittel

hexane EtOAc

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle