Sodium Hydroxide → (E)-3-[2-n-Butyl-1-[(2-chlorophenyl)methyl]-4-hydroxymethyl-1H-imidazol-5-yl]-2-benzyl-2-propenoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-4-t-butyldimethylsilyloxymethyl-1H-imidazol-5-yl]-2-benzyl-2-propenoate (167 mg, 0.287 mmol) in absolute ethanol (3 mL) was treated portionwise at 6 hour intervals with 10% sodium hydroxide solution (3×1 mL). After being stirred overnight at 25° C., the reaction was heated to 50° C. for 4 hours, then concentrated in vacuo. The residual product was take0 up in water, acidified to pH 5-6 and extracted with methylene chloride. The isolated, dried, concentrated product was triturated with methanol/ether to provide 78 mg (62%) of the title compound; mp 176°-179° C. (d).

Provenance & Evidence