Sodium hydride → HCID 44209617, compound

Participants

Reaction Steps

The procedure of Example 1(iv-v) was used. From 0.9 g (3.05 mmol) of 2-n-butyl-1-(2-chloro-6-fluorophenyl)-methyl-1H-imidazol-5-carboxaldehyde, 3 g (11 mol) of trimethyl benzylphosphonoacetate, 0.28 g of sodium hydride and glyme (12 mL) held at 60° C. for 1 hour was obtained, after chromatography over silica gel with 50% of hexane in ethyl acetate, 0.44 g (33%) of the trans isomer methyl (E)-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl} -1H-imidazol-5-yl]-2-benzyl-2-propenoate and 0.01 g (8%) of the corresponding cis or (Z)-isomer. The (E)-isomer(0.43 g, 0.98 mmol) was hydrolyzed to the acid and the product was crystallized from methanol to afford 0.38 g (91%) of (E)-3-[2-n-butyl-1-{(2-chloro-6-fluorophenyl)methyl}-1H-imidazol-5-yl]-2-benzyl-2-propenoic acid; mp 204°-206° C.

Provenance & Evidence