Propanal → 2,3-Dimethoxy-4-(1'-hydroxypropyl)pyridine

HRID 2246189

Reaktionsgleichung

Reaktionsgleichung von HRID 2246189
C([Li])CCC.[CH3:6][O:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][N:9]=1.[CH:16](=[O:19])[CH2:17][CH3:18]>O1CCCC1>[CH3:6][O:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([CH:16]([OH:19])[CH2:17][CH3:18])[CH:11]=[CH:10][N:9]=1

Komponenten

5

Edukt 3

HCID 527PropanalHCID 46578092,3-DimethoxypyridineHCID 178418339Butyllithium

Produkt 1

HCID 592179372,3-Dimethoxy-4-(1'-hydroxypropyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

n-Butyllithium (38.7 mL; 10 M in tetrahydrofuran (THF)) was dissolved in THF (600 mL) and cannulated to a solution of 2,3-dimethoxypyridine (3) (22.4 g; 161 mmol) in THF (200 mL) at −78° C. The reaction mixture was then warmed to 0° C. and stirred for 1 hour. The propionaldehyde (29.1 mL; 403 mmol) was added dropwise at −78° C. The reaction mixture was warmed to 25° C. and stirred for 16 hours. The reaction mixture was subsequently quenched with water and extracted with dichloromethane. The combined extracts were dried over sodium sulfate, concentrated under reduced pressure and purified by chromatography (SiO2; 2-10% ethyl acetate/hexane) to give the 2,3-dimethoxy-4-(1′-hydroxypropyl)pyridine (4) product (18.6 g; 59%) as a colorless oil.

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to 25° C.
  2. stirringstirred for 16 hours
  3. customThe reaction mixture was subsequently quenched with water
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by chromatography (SiO2; 2-10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6d1c1dd188e44332b8fbe90833677b2b
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687487B2

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