反応 #45776

反応方程式

citric acid

Triethylamine

cyclobutanecarbonyl chloride

2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile

→

compound

収率 85.0%

4-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclobutanecarboxylate

収率 85.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他the solvent was evaporated away under, reduced pressure
2. 2
   workup.ADDITIONEthyl acetate was added to the resulting residue
3. 3
   洗浄by washing with saturated brine
4. 4
   乾燥The organic layer was dried over anhydrous magnesium sulfate
5. 5
   その他the solvent was evaporated away under reduced pressure

実験手順

Under nitrogen atmosphere, 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (250 mg, 1.03 mmol) was dissolved in acetonitrile (0.10 ml), and cooled to 0° C. Triethylamine (244 μl, 1.75 mmol) and cyclobutanecarbonyl chloride (177 μl, 1.55 mmol) were dropwise added to the solution, followed by stirring at room temperature for 1 hour. 10% citric acid was added to the reaction liquid, and the solvent was evaporated away under, reduced pressure. Ethyl acetate was added to the resulting residue, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with ethyl acetate/hexane (1:4, v/v) gave the entitled compound (283 mg, 85%) as a white solid.

出典