Réaction #1552082

Équation de réaction

hydrochloric acid

3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole

1,4-butandiol monovinyl ether

dicylohexylmethylamine

→

title compound

Rendement 60.0%

1-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-ethanone

Rendement 60.0%

Solvants

ethyl acetate

n-butanol

Conditions de réaction

Traitement

1. 1
   Températureat reflux over night
2. 2
   TempératureAfter cooling
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for 1 h
4. 4
   FiltrationAfter filtration
5. 5
   Autrethe layers were separated
6. 6
   Extractionthe organic layer was extracted with 1 M HCl
7. 7
   Séchagedried (Na2SO4)
8. 8
   Autreevaporated in vacuum
9. 9
   AutrePurification of the residue on silica gel

Mode opératoire

A mixture of 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (500 mg), 1,4-butandiol-monovinyl ether (385 mg), 1,3-bis(diphenylphosphine)propane (dppp, 9 mg), palladium on charcoal (10%, 23 mg), dicylohexylmethylamine (259 mg) and n-butanol (3 mL) were stirred under an atmosphere of nitrogen at reflux over night. After cooling, ethyl acetate (30 mL) and aqueous hydrochloric acid (1 M, 20 mL) were added and the mixture was stirred at room temperature for 1 h. After filtration, the layers were separated, the organic layer was extracted with 1 M HCl, dried (Na2SO4) and evaporated in vacuum. Purification of the residue on silica gel afforded the title compound (270 mg, 60%).

Source