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

HRID 1157221ノート

反応式

HRID 1157221 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][OH:22])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[N:10]=[N:11][C:12]([Cl:18])=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=1.CC(C)=[O:25].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([OH:25])=[O:22])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[N:10]=[N:11][C:12]([Cl:18])=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=1

参加物

4

反応物 2

HCID 598345252-[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanolHCID 131709961Jones' reagent

生成物 1

HCID 59834443[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid収率 95%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
-1.5 °C

実験手順

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

後処理

  1. customprepared via standard method) slowly dropwise at −4° C
  2. customThe red reaction mixture
  3. customwas quenched with isopropanol
  4. filtrationThe resulting green suspension was filtered through celite
  5. washthe celite was washed well with ethyl acetate (600 mL)
  6. washThe filtrate was washed with water (600 mL)
  7. customThe organic layer was separated
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting solid was dried under vacuum overnight

出典と根拠

ORDレコード
ord-ad0cff39c5ff434a9591d48545505281
出典データセット
uspto-grants-2010_10
特許番号
US07807674B2

反応ノート

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