Ethyl beta-(1-methyl-2-ethyl-imidazol-5-yl)acrylate → Ethyl 3-(1-methyl-2-ethylimidazol-5-yl)propionate

HRID 863590Notes

Reaction equation

HRID 863590 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][N:4]=[C:3]1[CH2:14][CH3:15]>C(OCC)(=O)C.C(O)C.Cl.[Pd]>[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][N:4]=[C:3]1[CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 54480096Ethyl beta-(1-methyl-2-ethyl-imidazol-5-yl)acrylate

Product 1

HCID 22103420Ethyl 3-(1-methyl-2-ethylimidazol-5-yl)propionateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18938452ethyl acetate ethanol HClSolvent

Procedure

A mixture of ethyl β-(1-methyl-2-ethyl-imidazol-5-yl)acrylate (2.1 g, 10.1 mmol) and 1.1 g of 10% Pd/C in ethyl acetate/ethanol/HCl (1M in ethyl acetate; 50 ml/8 ml/8 ml) was hydrogenated under hydrogen (50 psi) for 2 h. The mixture was filtered through celite, the residue was washed with ethylene chloride/methanol (5:1, 2×), and the combined organic layer was concentrated in vacuo. The residue was basified with aqueous sodium bicarbonate solution, extracted with methylene chloride (4×), and the combined organic layer was dried over sodium sulfate and concentrated in vacuo. Upon chromatographic purification of the residue on 20 cm silica column (methylene chloride/methanol 50/1 - 15/1), 1.9 g (90%) of ethyl 3-(1-methyl-2-ethyl-imidazol-5-yl)propionate was isolated as a yellow oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe residue was washed with ethylene chloride/methanol (5:1, 2×)
  3. concentrationthe combined organic layer was concentrated in vacuo
  4. extractionextracted with methylene chloride (4×)
  5. dry with materialthe combined organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customUpon chromatographic purification of the residue on 20 cm silica column (methylene chloride/methanol 50/1 - 15/1)

Sources & evidence

ORD record
ord-b587ab3f838248aa96da318202eea147
Source dataset
uspto-grants-1998_02
Patent number
US05721261

Reaction notes

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