Réaction #2286306

Équation de réaction

6-[2,6-dichloro-4-(2-hydroxy-ethyl)-phenoxy]-4-isopropyl-2-methyl-pyridazin-3-one

6-[2,6-Dichloro-4-(2-hydroxyethyl)-phenoxy]-4-isopropyl-2-methyl-pyridazin-3-one

Jones Reagent

→

[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid

Rendement 19.0%

[3,5-Dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid

Rendement 19.0%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction mixture was then concentrated under vacuum
2. 2
   workup.ADDITIONThe resulting residue was diluted with ethyl acetate (25 mL) and water (20 mL)
3. 3
   workup.ADDITIONwas treated with sodium bisulfite (100 mg)
4. 4
   workup.STIRRINGThe resulting mixture was shaken
5. 5
   AutreThe aqueous layer was separated
6. 6
   Extractionwas re-extracted with ethyl acetate (25 mL)
7. 7
   Lavagewashed with a saturated aqueous sodium chloride solution
8. 8
   AutreThe organic layer was separated
9. 9
   Séchagedried with sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated under vacuum
12. 12
    AutreThe resulting solid was recrystallized from ethyl acetate
13. 13
    Autredried under vacuum overnight

Mode opératoire

A solution of 6-[2,6-dichloro-4-(2-hydroxy-ethyl)-phenoxy]-4-isopropyl-2-methyl-pyridazin-3-one (36) (330 mg, 0.92 mmol) in acetone (5 mL) was treated with Jones Reagent (0.51 mL of a 2.7M solution) slowly dropwise at 10° C. The resulting red reaction mixture was stirred at 11° C. for 30 min. The reaction mixture was then concentrated under vacuum. The resulting residue was diluted with ethyl acetate (25 mL) and water (20 mL) and was treated with sodium bisulfite (100 mg). The resulting mixture was shaken and turned from red to green. The aqueous layer was separated and was re-extracted with ethyl acetate (25 mL). The organic layers were combined and washed with a saturated aqueous sodium chloride solution. The organic layer was separated, dried with sodium sulfate, filtered, and concentrated under vacuum. The resulting solid was recrystallized from ethyl acetate and dried under vacuum overnight to afford [3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid (37) (70 mg, 19%) as a white solid; EI(+)-HRMS) m/z calcd for C16H16Cl2N2O4 (M+H)+ 371.0560, found 371.0561. Molecular Weight=371.2229; Exact Mass=370.0487

Source