Ethyl bromoacetate → 1,2-Di-[(ethoxycarbonyl)methyl]pyridinium bromide

HRID 1939251Notes

Reaction equation

HRID 1939251 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[Br-:13].[CH2:18]([O:17][C:15]([CH2:14][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:16])[CH3:19]

Participants

3

Reactant 2

HCID 7748Ethyl bromoacetateHCID 75960Ethyl 2-pyridylacetate

Product 1

HCID 214672521,2-Di-[(ethoxycarbonyl)methyl]pyridinium bromideYield 30%

Procedure

A mixture of ethyl 2-pyridylacetate (6.0 g, 0.036 mole) and ethyl bromoacetate (4.4 ml, 0.038 mole) was allowed to stand at room temperature for 72 h, during which time the product gradually crystallised out. The mixture was treated with acetone (80 ml) to dissolve unreacted starting materials and then filtered. The solid collected was dried under vacuum to afford 1,2-di-[(ethoxycarbonyl)methyl]pyridinium bromide as a beige solid (3.53 g, 30%).

Workup

  1. customthe product gradually crystallised out
  2. additionThe mixture was treated with acetone (80 ml)
  3. dissolutionto dissolve unreacted starting materials
  4. filtrationfiltered
  5. customThe solid collected
  6. customwas dried under vacuum

Sources & evidence

ORD record
ord-1e0d0fffc70c4cc094f4313a5d7738d0
Source dataset
uspto-grants-1997_12
Patent number
US05696129

Reaction notes

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