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

HRID 465842Notes

Reaction equation

HRID 465842 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'-carbomethoxybiphenyl-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): δ7.9-6.8 (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=7.4 Hz).

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-37e9c7f9571d4677bc6fdede93600257
Source dataset
uspto-grants-1992_10
Patent number
US05153197

Reaction notes

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