Water → 4-[(6-Chloro-3-pyridazinyl)oxy]benzenemethanol

HRID 347676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347676
[Cl:1][C:2]1[N:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[N:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 17859705HCID 17859705, Verbindung

Produkt 1

HCID 178597134-[(6-Chloro-3-pyridazinyl)oxy]benzenemethanolAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

3-Chloro-6-(4-formylphenoxy)pyridazine (4.06 g, 17.3 mmol) and 200 mL of methanol were mixed, and after sodium borohydride (654 mg, 17.3 mmol) was added under cooling with ice and stirring, the mixture was stirred for 15 minutes. Water was added to the reaction mixture and methanol was distilled off. The residue was poured into water, which was extracted with ethyl acetate. The extracted solution was washed with saturated brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:2 v/v) to obtain 3.10 g (76%) of the title compound as a colorless oily product.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 15 minutes
  3. distillationwas distilled off
  4. additionThe residue was poured into water, which
  5. extractionwas extracted with ethyl acetate
  6. washThe extracted solution was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=1:2 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-dadae83fcd9645f797ee40cdeb618f20
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176204B2

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