反应详情

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.

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