Imidazole → Ethyl 3-(imidazol-1-yl)-2-phenylpropanoate

HRID 569580

Reaction equation

HRID 569580 reaction equation
[C:1]1([C:7](=[CH2:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>O1CCCC1.CN(C)C(=N)N(C)C>[N:14]1([CH2:13][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 89651Ethyl 2-phenylacrylate

Product 1

HCID 13851116Ethyl 3-(imidazol-1-yl)-2-phenylpropanoateYield 81.9%

Reagents, catalysts & solvents 2

HCID 664601,1,3,3-TetramethylguanidineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-phenylprop-2-enoate (160 g, 0.45 mol), imidazole (36.7 g 0.54 mol) and tetramethylguanidine (2 g, 0.017 mol) in dry tetrahydrofuran (1 L) was heated at reflux temperature for 3 hours. The solvent was removed under reduced pressure and the residue was dissolved in dilute hydrochloric acid. The resulting aqueous solution was washed with ether, basified with dilute aqueous sodium hydroxide and extracted with chloroform. The organic phase was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield ethyl 3-(imidazol-1-yl)-2-phenylpropanoate (90 g).

Workup

  1. temperatureat reflux temperature for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in dilute hydrochloric acid
  4. washThe resulting aqueous solution was washed with ether
  5. extractionextracted with chloroform
  6. customThe organic phase was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8981f31dea284a06bd2aca2b271f6a5c
Source dataset
uspto-grants-1988_03
Patent number
US04732989

Linked notes

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