반응 #70843

반응 방정식

Water

4-methylpyrimidine

NaH

ethyl 4-fluorobenzoate

→

desired compound

수율 48.0%

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

수율 48.0%

용매

hexane EtOAc

DMF

반응 조건

후처리

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

실험 절차

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%).

출처