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

HRID 543301

Reaction equation

HRID 543301 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-bb12279ba71441bcae3090bbaa4ea332
Source dataset
uspto-grants-1987_04
Patent number
US04661602

Linked notes

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