Réaction #78832

Équation de réaction

potassium carbonate

dicyclohexylcarbodiimide

1-cyclopentyl-5-hydroxy-1H-pyrazole

2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid

→

4-[2-Methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-cyclopentyl-5-hydroxy-1H-pyrazole

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   FiltrationSolid components were then filtered off
2. 2
   Températurerefluxed for 4 hours
3. 3
   AutreThe solvent was removed
4. 4
   Lavagethe mixture was washed with ethyl acetate
5. 5
   Extractionextracted with methylene chloride
6. 6
   workup.DISTILLATIONThe solvent of the resulting organic phase was distilled off
7. 7
   Filtrationinsoluble components were filtered off
8. 8
   Autrethe resulting precipitate was separated off
9. 9
   Autredried

Mode opératoire

1.9 g (9.4 mmol) of dicyclohexylcarbodiimide and 1.3 g (8.8 mmol) of 1-cyclopentyl-5-hydroxy-1H-pyrazole were added to a solution of 2.5 g (8.8 mmol) of 2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid in 100 ml of dioxane, and the mixture was stirred at room temperature for 12 hours. Solid components were then filtered off and the filtrate was admixed with 1.5 g (10 mmol) of potassium carbonate and refluxed for 4 hours. The solvent was removed, the residue was then taken up in water and the mixture was washed with ethyl acetate, and then adjusted to pH 3 using 10% strength hydrochloric acid and extracted with methylene chloride. The solvent of the resulting organic phase was distilled off, the residue was taken up in 300 ml of aqueous potassium carbonate solution, insoluble components were filtered off, the pH was adjusted to 3 using 10% strength hydrochloric acid and the resulting precipitate was separated off and dried. Yield: 1.5 g (42% of theory) of 4-[2-methyl-3-(4,5-dihydro-isoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-cyclopentyl-5-hydroxy-1H-pyrazole

Source