Reaktion #2286295

Reaktionsgleichung

2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol

2-[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol

Jones Reagent

→

[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid

Ausbeute 95.0%

[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid

Ausbeute 95.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared via standard method) slowly dropwise at −4° C
2. 2
   SonstigeThe red reaction mixture
3. 3
   Sonstigewas quenched with isopropanol
4. 4
   FiltrationThe resulting green suspension was filtered through celite
5. 5
   Waschenthe celite was washed well with ethyl acetate (600 mL)
6. 6
   WaschenThe filtrate was washed with water (600 mL)
7. 7
   SonstigeThe organic layer was separated
8. 8
   Trocknendried with magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated
11. 11
    SonstigeThe resulting solid was dried under vacuum overnight

Vorschrift

A solution of 2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol (17) (8.4 g, 23.2 mmol) in acetone (270 mL) was treated with Jones Reagent (34.8 mL of a 2.7 M solution, prepared via standard method) slowly dropwise at −4° C. The resulting red reaction mixture was stirred for 1 h at −3 to 0° C. The red reaction mixture was quenched with isopropanol. The resulting green suspension was filtered through celite and the celite was washed well with ethyl acetate (600 mL). The filtrate was washed with water (600 mL) and a saturated aqueous sodium chloride solution (300 mL). The organic layer was separated, dried with magnesium sulfate, filtered, and concentrated. The resulting solid was dried under vacuum overnight to afford [3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid (18) (8.3 g, 95%) as a white solid; LRMS for C15H15Cl3N2O3 (M+) m/z=377. Molecular Weight=377.6574; Exact Mass=376.0148

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