Furfural → 5-Furan-2-yl-3-hydroxy-1-(3-imidazol-1-yl-propyl)-4-pentyl-1,5-dihydro-pyrrol-2-one

HRID 2060320Notes

Reaction equation

HRID 2060320 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=O.C([O:19][C:20](=O)[C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])C>C(O)C>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]1[N:9]([CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:20](=[O:19])[C:21]([OH:28])=[C:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 7362FurfuralHCID 787361H-Imidazole-1-propanamineHCID 10888659Ethyl 2-oxooctanoate

Product 1

HCID 579240955-Furan-2-yl-3-hydroxy-1-(3-imidazol-1-yl-propyl)-4-pentyl-1,5-dihydro-pyrrol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

3-Imidazol-1-yl-propylamine (1 mmol) and Furan-2-carbaldehyde (1 mmol) were added to ethanol (5 ml). After 30 min 2-Oxo-octanoic acid ethyl ester (1 mmol) was added. The reaction was heated to 50° C. and stirred for 24 h. After evaporation of the solvent the residue was purified with chromatographic methods.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas purified with chromatographic methods

Sources & evidence

ORD record
ord-1744b439609d4f2e86b9c88172d0c475
Source dataset
uspto-grants-2012_10
Patent number
US08278345B2

Reaction notes

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