Sodium ethoxide → Diethyl 1-benzyl-2-ethoxymethylimidazole-4,5-dicarboxylate

HRID 265191Notes

Reaction equation

HRID 265191 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:10]=[C:9]1[CH2:23]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:25][CH2:26][CH3:27].[Na+]>C(O)C>[CH2:1]([N:8]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:10]=[C:9]1[CH2:23][O:25][CH2:26][CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 19036091Diethyl 1-benzyl-2-bromomethylimidazole-4,5-dicarboxylate

Product 1

HCID 19036277Diethyl 1-benzyl-2-ethoxymethylimidazole-4,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1.80 g of diethyl 1-benzyl-2-bromomethylimidazole-4,5-dicarboxylate [prepared as described in Preparation42(ii)] in 50 ml of ethanol was added dropwise to a solution of sodium ethoxide in ethanol (prepared from 0.18 g of sodium and 50 ml of ethanol), and the resulting mixture was left at room temperature for 13 hours. At the end of this time, a procedure similar to that described in Preparation 42(iii) was repeated, and the residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.14 g of the title compound as a syrup.

Workup

  1. customthe residue was purified by column chromatography through silica gel
  2. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-9d8864ab4c68486280f97472df452b30
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

Loading…