Reaktion #2286306

Reaktionsgleichung

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

Ausbeute 19.0%

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

Ausbeute 19.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe 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
   SonstigeThe aqueous layer was separated
6. 6
   Extraktionwas re-extracted with ethyl acetate (25 mL)
7. 7
   Waschenwashed with a saturated aqueous sodium chloride solution
8. 8
   SonstigeThe organic layer was separated
9. 9
   Trocknendried with sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated under vacuum
12. 12
    SonstigeThe resulting solid was recrystallized from ethyl acetate
13. 13
    Sonstigedried under vacuum overnight

Vorschrift

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

Quelle