반응 #358347

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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

수율 95.0%

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

수율 95.0%

용매

acetone

반응 조건

후처리

1. 1
   기타prepared via standard method) slowly dropwise at −4° C
2. 2
   기타The red reaction mixture
3. 3
   기타was quenched with isopropanol
4. 4
   여과The resulting green suspension was filtered through celite
5. 5
   세척the celite was washed well with ethyl acetate (600 mL)
6. 6
   세척The filtrate was washed with water (600 mL)
7. 7
   기타The organic layer was separated
8. 8
   건조dried with magnesium sulfate
9. 9
   여과filtered
10. 10
    농축concentrated
11. 11
    기타The resulting solid was dried under vacuum overnight

실험 절차

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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