Reaktion #45620

Reaktionsgleichung

N-(4-Acetyl-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)cyclopropanecarboxamide

pyridinium p-toluenesulfonate

→

compound

Ausbeute 71.5%

6-Acetyl-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Ausbeute 71.5%

Lösungsmittel

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONadded
2. 2
   Temperaturby heating
3. 3
   Temperaturunder reflux for 21 hours
4. 4
   Waschenwashed with water and saturated brine
5. 5
   TrocknenThe obtained organic layer was dried over anhydrous sodium sulfate
6. 6
   Sonstigethe solvent was evaporated away under reduced pressure
7. 7
   Wascheneluted with a mixed solvent of n-hexane/ethyl acetate (3:1

Vorschrift

N-(4-Acetyl-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)cyclopropanecarboxamide (I-81) (200 mg, 0.72 mmol) was dissolved in toluene (4 ml), pyridinium p-toluenesulfonate (40 mg, 0.14 mmol) was, added, followed by heating under reflux for 21 hours. After cooling to room temperature, this was diluted with ethyl acetate, washed with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, eluted with a mixed solvent of n-hexane/ethyl acetate (3:1, v/V) to obtain the entitled compound (133 mg, 71%) as a white solid.

Quelle