Ethylene Glycol → 3-Chloro-5-(2-hydroxyethoxy)pyridine

HRID 1266970Notes

Reaction equation

HRID 1266970 reaction equation
[Na].[CH2:2]([OH:5])[CH2:3][OH:4].[Cl:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11](Cl)[CH:12]=1.[OH-].[Na+]>CS(C)=O>[Cl:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([O:4][CH2:3][CH2:2][OH:5])[CH:12]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 171533,5-DichloropyridineHCID 5360545Sodium

Product 1

HCID 115573693-Chloro-5-(2-hydroxyethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of sodium (2.0 g, 89.5 mmol) and ethylene glycol (50 ml) was stirred at 70° C. for 30 min. 3,5-Dichloropyridine (11.0 g, 74.5 mmol) and dimethyl sulfoxide (50 ml) were added to the crude mixture. The crude mixture was stirred for 10 h at 110° C. Aqueous sodium hydroxide (100 ml) was added and the crystals were filtered. Yield 8.0 g, 51%.

Workup

  1. filtrationthe crystals were filtered

Sources & evidence

ORD record
ord-7549f0b6aafc4058a7967b2f1d0530fb
Source dataset
uspto-grants-2003_04
Patent number
US06552012B2

Reaction notes

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