Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl (E)-3-(4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazol-5-yl)-2-propenate

HRID 1828812Notes

Reaction equation

HRID 1828812 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:18])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[Cl:17])[C:6]=1[CH:7]=O.C1(P(=[CH:38][C:39]([O:41][CH3:42])=[O:40])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH3:18])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[Cl:17])[C:6]=1/[CH:7]=[CH:38]/[C:39]([O:41][CH3:42])=[O:40]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 155242134-Chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazole-5-carbaldehyde

Product 1

HCID 15524214methyl (E)-3-(4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazol-5-yl)-2-propenateYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazole 5-carbaldehyde (1.01 g) in tetrahydrofuran (10 ml) was added methyl (triphenylphosphoranylidene)acetate (1.27 g) and the mixture was refluxed under heating for 4 hr. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give methyl (E)-3-(4-chloro-1-(2-chloro-4-iodobenzyl)-2-methylimidazol-5-yl)-2-propenate (974 mg) as a white powder.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hr
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-7e3882ecb0c0424d851282247591c96b
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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