Hydrochloric Acid → [6-(3-Chloro-4-fluoro-phenyl)-pyridazin-4-yl]-methanol

HRID 891947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891947
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[N:11][CH:12]=[C:13]([CH2:15][O:16]COC)[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl.O.C(OCC)(=O)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[N:11][CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 22240138HCID 22240138, Verbindung

Produkt 1

HCID 22240129[6-(3-Chloro-4-fluoro-phenyl)-pyridazin-4-yl]-methanolAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3-(3-Chloro-4-fluoro-phenyl)-5-methoxymethoxymethyl-pyridazine (0.06 g, 0.21 mmol) was dissolved in dioxane (2 ml) and treated with 1N HCl (0.2 ml, 0.2 mmol). The reaction mixture was refluxed for 1.5 hours then cooled to room temperature. Water and ethyl acetate were added. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed over silica gel (hexane-ethylacetate 1:1 then 2:8) to provide [6-(3-chloro-4-fluoro-phenyl)-pyridazin-4-yl]-methanol (13 mg, 26%) as a light yellow solid, MS: m/e=239.2 (M+H+).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 1.5 hours
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed over silica gel (hexane-ethylacetate 1:1

Quellen und Nachweise

ORD-Eintrag
ord-18131378fce447d2b10a6396fc58823d
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005432B2

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