Toluene → methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(3,4-methylenedioxyphenyl)methyl-2-propenoate

Participants

Reaction Steps

A solution of methyl 3-acetoxy-3-[2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-yl]-2-(3,4-methylenedioxyphenyl)methylpropanoate (1.36 g, 2.58 mmol), 1,8-diazobicyclo[5,4,0]undec-7-ene (1 mL, 6.48 mmol) and toluene (10 mL) was heated at 90 ° C. for 18 hours under argon. The cooled reaction mixture was diluted with ether, the solution was filtered and the filtrate was concentrated. Chromatography of the product over silica gel with a gradient of ethyl acetate in hexane provided 1.1 g (87%) of methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5yl]-2-(3,4-methylenedioxyphenyl)methyl-2-propenoate as a low melting solid whose NMR showed the E or trans relationship of the ester group to the imidazole ring.

Provenance & Evidence