Dichloroacetic Acid → HCID 72545205, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 228 mg of NaH (60% dispersion in mineral oil) and 18 mg of 18-crown-6 ether in 8 ml of anhydrous dioxane, a solution of 2.3 ml of a solution of dichloroacetic acid (1 M) in anhydrous dioxane was slowly added at room temperature. The reaction mixture was heated to 60° C. and a solution of 504 mg of 2-(Dicyclohexyl-hydroxy-methyl)-5-pyrrol-1-yl-phenol in 6 mL anhydrous dioxane was added and stirred at 95° C. for 6 h. After cooling to 0° C., the reaction mixture was quenched with 2 ml of isopropanol and poured on ice. The aqueous phase was extracted with ether, then acidified with HCl (2 M, to pH 1), and extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a white solid. Yield: 118 mg.

Provenance & Evidence