N-(2-Hydroxyethyl)imidazole → 2-(1H-Imidazol-1-yl)ethyl methoxyacetate

HRID 723280Notes

Reaction equation

HRID 723280 reaction equation
[N:1]1([CH2:6][CH2:7][OH:8])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:9][O:10][CH2:11][C:12](OC)=[O:13]>C[O-].[Na+].C1(C)C=CC=CC=1>[CH3:9][O:10][CH2:11][C:12]([O:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:13]

Participants

5

Reactant 2

HCID 74168N-(2-Hydroxyethyl)imidazoleHCID 80507Methyl methoxyacetate

Product 1

HCID 218725332-(1H-Imidazol-1-yl)ethyl methoxyacetateYield 90.2%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 1140TolueneSolvent

Procedure

In a nitrogen atmosphere, a mixture of 112 g of 2-(1H-imidazol-1-yl)ethanol, synthesized in Synthesis Example 1, 156 g of methyl methoxyacetate, 3.0 g of sodium methoxide, and 200 g of toluene was heated under reflux for 20 hours while distilling off the methanol formed during the reaction. The solvent was distilled off in vacuo. Purification by vacuum distillation gave 166 g of 2-(1H-imidazol-1-yl)ethyl methoxyacetate (boiling point 126° C./27 Pa, yield 90%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. distillationwhile distilling off the methanol
  4. customformed during the reaction
  5. distillationThe solvent was distilled off in vacuo
  6. customPurification
  7. distillationby vacuum distillation

Sources & evidence

ORD record
ord-39cdc5cb1477411e99c388126cee1a67
Source dataset
uspto-grants-2006_11
Patent number
US07141351B2

Reaction notes

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