Lithium hydroxide, monohydrate → tert-butyl(E)-5-chloro-2-{1-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]methylidene}valerate

Participants

Reaction Steps

3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (2.29 g) and tert-butyl 5-chloro-2-(diethoxyphosphoryl)valerate (3.68 g) were dissolved in a mixed solvent of THF (30 mL) and ethanol (10 mL). Lithium hydroxide monohydrate (1.41 g) was added to the reaction solution at room temperature, and the reaction solution was stirred at room temperature for 18 hours. Saturated sodium bicarbonate water was added to the reaction solution, followed by extraction with ethyl acetate. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system), solidified with tert-butyl methyl ether and heptane, and separated by filtration to obtain 1.96 g of the title compound. The property values of the compound are as follows.

Provenance & Evidence