Reaction #2286306

Reaction equation

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

Yield 19.0%

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

Yield 19.0%

Solvents

acetone

Conditions

Workup

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
   OtherThe aqueous layer was separated
6. 6
   Extractionwas re-extracted with ethyl acetate (25 mL)
7. 7
   Washwashed with a saturated aqueous sodium chloride solution
8. 8
   OtherThe organic layer was separated
9. 9
   Dryingdried with sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated under vacuum
12. 12
    OtherThe resulting solid was recrystallized from ethyl acetate
13. 13
    Otherdried under vacuum overnight

Procedure

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