Methyl methoxyacetate → HCID 21872629, compound

HRID 723296Notes

Reaction equation

HRID 723296 reaction equation
[N:1]1([CH2:10][CH2:11][OH:12])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:13][O:14][CH2:15][C:16](OC)=[O:17].C[O-].[Na+]>COCCOCCOC>[CH3:13][O:14][CH2:15][C:16]([O:12][CH2:11][CH2:10][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)=[O:17]

Participants

5

Reactant 3

HCID 80507Methyl methoxyacetateHCID 2281312-(1H-Benzimidazol-1-yl)ethan-1-olHCID 10942334Sodium Methoxide

Product 1

HCID 21872629HCID 21872629, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

In a nitrogen atmosphere, a mixture of crude 2-(1H-benzimidazol-1-yl)ethanol as prepared in Synthesis Example 1, 156 g of methyl methoxyacetate, 3.0 g of sodium methoxide, and 200 g of diglyme was heated under reflux for 20 hours while distilling off the methanol formed during the reaction. The solvent was distilled off in vacuo. The reaction mixture was subjected to conventional aqueous work-up and then purified by column chromatography, obtaining 2-(1H-benzimidazol-1-yl)ethyl methoxyacetate (yield 65%).

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. custompurified by column chromatography

Sources & evidence

ORD record
ord-3d5cedc5a9fa40f2b2ffaef8b6218eef
Source dataset
uspto-grants-2006_11
Patent number
US07141352B2

Reaction notes

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