Triethyl 2-phosphonopropionate → HCID 67849290, compound

HRID 1033881Notes

Reaction equation

HRID 1033881 reaction equation
[Na].[CH3:2][CH2:3][O:4][C:5]([CH:7](P(OCC)(OCC)=O)[CH3:8])=[O:6].[CH2:17]([C:21]1[N:22]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:23]([CH:26]=O)=[CH:24][N:25]=1)[CH2:18][CH2:19][CH3:20]>C(O)C>[CH2:17]([C:21]1[N:22]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:23](/[CH:26]=[C:7](\[CH3:8])/[C:5]([O:4][CH2:3][CH3:2])=[O:6])=[CH:24][N:25]=1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 107155Triethyl 2-phosphonopropionateHCID 5360545SodiumHCID 101075301H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]-

Product 1

HCID 67849290HCID 67849290, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Ethanol (5 mL) was treated with sodium metal (0.101 g, 0.0044 g-atom), then triethyl 2-phosphonopropionate (0.953 g, 0.004 mol) in ethanol (2 mL) was added. After 5 minutes a solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde (1.1 g, 0.004 mol) in ethanol (2 mL) was added to give an initial exotherm The reaction mixture was stirred at ambient temperature under argon for 2 hours, concentrated in vacuo and the residue partitioned between water and ethyl acetate. The extract was washed, dried, and concentrated. The crude product was flash chromatographed over silica gel with an ethyl acetate/hexane gradient to provide ethyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-methyl-2-propenoate (0.85 g, 59%) as an oil; NMR (NOE) was consistent with the structure.

Workup

  1. customto give an initial exotherm The reaction mixture
  2. concentrationconcentrated in vacuo
  3. customthe residue partitioned between water and ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. concentrationconcentrated
  7. customchromatographed over silica gel with an ethyl acetate/hexane gradient

Sources & evidence

ORD record
ord-06c5b5b3cdb14428a651e0afe02e103e
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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