Hydrochloric Acid → 3-Pyridinebutanol

HRID 1656311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656311
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][CH2:9][CH2:10][O:11]C2CCCCO2)[CH:2]=1.Cl>CO.O.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:2]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 539444502-[4-(3-Pyridyl)but-3-enoxy]tetrahydropyran

Produkt 1

HCID 134191363-PyridinebutanolAusbeute 241,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

10 g (43 mmol) of 2-[4-(3-pyridyl)but-3-enoxy]tetrahydropyran in 200 ml of methanol/water 1:1 (v/v) is acidified by 2N hydrochloric acid and hydrogenated for 16 hours over 2 g 10% palladium on carbon. After filtration, the solvent is removed, the remaining residue is neutralized by saturated aqueous bicarbonate, and the product is extraced with several portions of ether. Purification of the crude product by column chromatography on silica gel yields 15.7 g (87%) of 4-(3-pyridyl)but-Anol as colourless viscous oil. (C9H13NO; F.W. 151.2).

Aufarbeitung

  1. filtrationAfter filtration
  2. customthe solvent is removed
  3. customPurification of the crude product by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f25440d9186642c1840fccd1a2b923db
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05254549

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