Reaktion #553024

Reaktionsgleichung

1-(2'-carbomethoxybiphenyl-4-yl)methyl-2-butyl-4-chloroimidazole-5-carboxaldehyde

1-triphenylphosphoran-ylidene-2-propanone

benzene

→

desired compound

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

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle