Реакция #2286295

Уравнение реакции

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

Выход 95.0%

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

Выход 95.0%

Растворители

acetone

Условия реакции

Обработка

1. 1
   Другоеprepared via standard method) slowly dropwise at −4° C
2. 2
   ДругоеThe red reaction mixture
3. 3
   Другоеwas quenched with isopropanol
4. 4
   ФильтрацияThe resulting green suspension was filtered through celite
5. 5
   Промывкаthe celite was washed well with ethyl acetate (600 mL)
6. 6
   ПромывкаThe filtrate was washed with water (600 mL)
7. 7
   ДругоеThe organic layer was separated
8. 8
   Сушкаdried with magnesium sulfate
9. 9
   Фильтрацияfiltered
10. 10
    Концентрированиеconcentrated
11. 11
    ДругоеThe resulting solid was dried under vacuum overnight

Методика

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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