Ethylene Glycol → 3-(Pyridin-4-yloxy)propan-1-OL

Reaktionsgleichung

Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([OH:11])[CH2:9]O.[OH-:12].[Na+].[CH3:14]S(C)=O>>[OH:12][CH2:14][CH2:9][CH2:8][O:11][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Komponenten

Edukt 4

HCID 174Ethylene Glycol

HCID 679Dimethyl Sulfoxide

HCID 122884-Chloropyridine

HCID 14798Sodium Hydroxide

Produkt 1

HCID 219360073-(Pyridin-4-yloxy)propan-1-OLAusbeute 45 %

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 4-chloropyridine (7 g, 47 mmol), ethylene glycol (17.9 g, 235 mmol) and sodium hydroxide (4.67 g, 195 mmol) in DMSO (80 ml) was heated at 100° C. for 24 hours. Most of the solvent was removed by evaporation and the residue was diluted with ice water. The aqueous mixture was extracted with ethyl acetate, the extracts combined, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3) to give 4-(3-hydroxypropoxy)pyridine (3.2 g, 45%).