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

Reaction equation

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

Participants

Reactant 4

HCID 174Ethylene Glycol

HCID 679Dimethyl Sulfoxide

HCID 122884-Chloropyridine

HCID 14798Sodium Hydroxide

Product 1

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

Conditions

Temperature: 100 °C

Procedure

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%).