Methylparaben → HCID 68513427, compound

Participants

Reaction Steps

To a solution (15 mL) of cyclohexyl{4-methyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}methanol (0.81 g) synthesized in Example 298 (6) in tetrahydrofuran were added methyl 4-hydroxybenzoate (0.4 g), tributylphosphine (1.2 mL) and dipiperidide azodicarboxylate (1.2 g) with stirring under ice-cooling. The ice bath was removed, and the reaction mixture was stirred at room temperature overnight. Hexane was added to the reaction mixture, and the precipitate was filtered through celite. Water was added to the filtrate and the mixture was extracted with ethyl acetate. The extract was purified by silica gel chromatography (ethyl acetate:hexane=1:1, volume ratio) to give a methyl ester form of the title compound (0.96 g). This was dissolved in ethanol (5 mL), 1N sodium hydroxide (4 mL) was added at 60° C. and the mixture was stirred for 1 hr. Ethanol was evaporated under reduced pressure, and 1N hydrochloric acid (4 mL) was added to the residue to give the title compound (0.88 g, 80%) as an amorphous form.

Provenance & Evidence