Benzene → 4-[1-(2'-Carbomethoxybiphenyl-4-yl)methyl-2-butyl-4-chloroimidazol-5-yl]-3-buten-2-one

HRID 653931Notes

Reaction equation

HRID 653931 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22](C=O)=[C:21]([Cl:25])[N:20]=[C:19]2[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:13][CH:12]=1)([O:3][CH3:4])=[O:2].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:37][C:38](=[O:40])[CH3:39])C=CC=CC=1.[CH:53]1C=CC=CC=1>>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][N:18]2[C:22]([CH:53]=[CH:37][C:38](=[O:40])[CH3:39])=[C:21]([Cl:25])[N:20]=[C:19]2[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:15][CH:16]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 3

HCID 241BenzeneHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 156980691-(2'-Carbomethoxybiphenyl-4-yl)methyl-2-butyl-4-chloroimidazole-5-carboxaldehyde

Product 1

HCID 538198364-[1-(2'-Carbomethoxybiphenyl-4-yl)methyl-2-butyl-4-chloroimidazol-5-yl]-3-buten-2-one

Procedure

A mixture of 0.5 g of 1-(2'-carbomethoxybi-phenyl-4-yl)methyl-2-butyl-4-chloroimidazole-5-carboxaldehyde and 0.04 g of 1-triphenylphosphoran-ylidene-2-propanone in 20 mL of benzene was refluxed for 16 hours. The reaction mixture was concentrated to give an oily residue which was purified by flash chromatography on silica gel (hexane:ethyl acetate=1:1 elution). The desired compound was obtained as a thick yellowish liquid, 0.46 g; NMR (200 MHz, CDCl3): δ 7.9-6.8 (m, 10H); 5.24 (s, 2H); 3.62 (s, 3H); 3.62 (s, 3H); 2.69 (t, 2H, J=7.4 Hz); 2.26 (s, 3H); 1.72 (m, 2H); 1.38 (m, 2H); 0.91 (t, 3H, J=7.4Hz).

Workup

  1. temperaturewas refluxed for 16 hours
  2. concentrationThe reaction mixture was concentrated
  3. customto give an oily residue which
  4. customwas purified by flash chromatography on silica gel (hexane:ethyl acetate=1:1 elution)

Sources & evidence

ORD record
ord-17fe3b28dfb44f4ca89cce520d3d34fd
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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