Ethylene Glycol → 2-[(6-Chloropyrimidin-4-yl)oxy]ethan-1-ol

HRID 1082307Notes

Reaction equation

HRID 1082307 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH2:9]([OH:12])[CH2:10][OH:11].[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([O:11][CH2:10][CH2:9][OH:12])[CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 125648862-[(6-Chloropyrimidin-4-yl)oxy]ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4,6-dichloropyrimidine (5.0 g), ethylene glycol (100 ml) and tetrahydrofuran (100 ml) is added sodium hydride (60% dispersion-type, 1.34 g) under ice-cooling. The mixture is stirred at the same temperature for two hours, and evaporated to remove the solvent. The residue is extracted with ethyl acetate, and the ethyl acetate extract is dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1~2:1) to give 2-(6-chloropyrimidin-4-yloxy)ethanol (5.67 g) as an oily product.

Workup

  1. temperaturecooling
  2. customevaporated
  3. customto remove the solvent
  4. extractionThe residue is extracted with ethyl acetate
  5. extractionthe ethyl acetate extract
  6. customis dried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1~2:1)

Sources & evidence

ORD record
ord-3c47ebdae8dc466e868cd4f855f43a41
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Reaction notes

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