Lithium Hydroxide → 4-[3-(Pyridin-4-yl)propyloxy]benzoic acid

HRID 265884

Reaktionsgleichung

Reaktionsgleichung von HRID 265884
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=2)=[CH:3][CH:2]=1.[Li+].[OH-].C1COCC1>C(Cl)Cl.CO.CC(O)=O>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 53832197Methyl 4-[3-(4-pyridinyl)propoxy]benzoate

Produkt 1

HCID 190341454-[3-(Pyridin-4-yl)propyloxy]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21877243DCM MeOH AcOHLösungsmittel

Versuchsvorschrift

A solution of 19-4 (3.2 g, 11.9 mmol), 1N LiOH (25 mL), and THF (50 mL) was stirred overnight at ambient temperature. After 20 h, the solution was washed with EtOAc and then acidified with 10% KHSO4 to give a suspension of white solid. The aqueous portion was extracted with CHCl3 and then the aqueous portion containing the solid was filtered. After drying the solid at 50° C. for 3 h, 19-5 was obtained. Rf 0.47 (silica, 10/1/1 CH2Cl2 /CH3OH/AcOH).

Aufarbeitung

  1. washthe solution was washed with EtOAc
  2. customto give
  3. additiona suspension of white solid
  4. extractionThe aqueous portion was extracted with CHCl3
  5. additionthe aqueous portion containing the solid
  6. filtrationwas filtered
  7. customAfter drying the solid at 50° C. for 3 h
  8. custom19-5 was obtained

Quellen und Nachweise

ORD-Eintrag
ord-d4fc639ea6b44fd5b7b8b593e7e817de
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648368

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