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

HRID 1599033Notes

Reaction equation

HRID 1599033 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, 1.34 g) under ice-cooling, and the mixture is stirred at the same temperature for two hours, and evaporated under reduced pressure to remove the solvent. The residue is extracted with ethyl acetate, and the 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 under reduced pressure
  3. customto remove the solvent
  4. extractionThe residue is extracted with ethyl acetate
  5. customthe extract is dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=5:1~2:1)

Sources & evidence

ORD record
ord-6401720eefca4e5eaf04bf174ac7fb18
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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