3-Pyridinecarboxaldehyde → 2-Methoxy-5-(pyrid-3-ylhydroxymethyl)pyridine

HRID 34912

Reaktionsgleichung

Reaktionsgleichung von HRID 34912
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C([Li])CCC.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[O:22])[CH:16]=1.[Cl-].[NH4+]>CCCCCC.CCOCC.O>[CH3:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([CH:21]([C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)[OH:22])=[CH:7][N:6]=1

Komponenten

8

Edukt 4

HCID 103713-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 27348955-Bromo-2-methoxypyridineHCID 178418339Butyllithium

Produkt 1

HCID 198517782-Methoxy-5-(pyrid-3-ylhydroxymethyl)pyridineAusbeute 23,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

5-Bromo-2-methoxypyridine (188 g) was added over 30 minutes to a 1.55 molar solution of n-butyllithium in hexane (770 ml) and ether (1200 ml) stirred at -50° C. The suspension was stirred for 1 hour when pyridine-3-carboxaldehyde (112 g) in ether (200 ml) was added over 30 minutes. The solution was stirred for 3.5 hr and then allowed to warm to ambient temperature. Saturated ammonium chloride solution (100 ml) and water (2 L) was added and the solution was concentrated to ca. 2.5 L in vacuo. Chloroform (3 L) was added and the title compound (41.3 g) was collected by filtration. The chloroform layer was separated, dried over magnesium sulphate and the solvent was removed under reduced pressure. The residue was treated with chloroform (200 ml) and filtered to give a second crop of the product (51.01 g). Recrystallisation from isopropanol/ether gave the title compound, m.p. 129°-130° C.

Aufarbeitung

  1. additionwas added over 30 minutes
  2. stirringThe solution was stirred for 3.5 hr
  3. temperatureto warm to ambient temperature
  4. concentrationthe solution was concentrated to ca. 2.5 L in vacuo
  5. additionChloroform (3 L) was added
  6. filtrationthe title compound (41.3 g) was collected by filtration
  7. customThe chloroform layer was separated
  8. dry with materialdried over magnesium sulphate
  9. customthe solvent was removed under reduced pressure
  10. additionThe residue was treated with chloroform (200 ml)
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-dc204285c2f4451f98963c40642279f0
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04764519

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