Réaction #45806

Équation de réaction

sodium hydrogencarbonate

N-(5-Cyano-2-fluoro-4-hydroxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide

ethyl acetate

→

compound

Rendement 90.0%

2-tert-Butyl-4-fluoro-6-methyl-5-phenyl-1,3-benzoxazole-7-carbonitrile

Rendement 90.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   AutreThe reaction liquid
2. 2
   Températurewas heated
3. 3
   Températureunder reflux under nitrogen atmosphere for 4.5 hours
4. 4
   AutreThe aqueous layer was separated
5. 5
   Extractionthis was extracted with ethyl acetate
6. 6
   LavageThe organic layer was washed with saturated brine
7. 7
   Séchagedried over anhydrous sodium sulfate
8. 8
   AutreThe insoluble matter was separated by filtration
9. 9
   Autrethe solvent was evaporated away
10. 10
    Autrethe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=9:1)

Mode opératoire

N-(5-Cyano-2-fluoro-4-hydroxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide (I-238) (124 mg, 0.38 mol) was dissolved in toluene (5 ml), and at room temperature, paratoluenesulfonic acid monohydrate (20 mg, 0.11 mmol) was added. The reaction liquid was heated under reflux under nitrogen atmosphere for 4.5 hours. After cooling to room temperature, the solution was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was separated, this was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=9:1) to obtain the entitled compound (106 mg, 90%) as a white solid.

Source