Hydrochloric Acid → 4-{(3E)-4-{2-[(4-tert-Butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 1.1 g (1.97 mmol) of methyl-4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate from Example 102A in 7.20 ml of THF and 3.60 ml of water is mixed with 189 mg (7.89 mmol) of lithium hydroxide and stirred at 60° C. for 12 h. The reaction mixture is adjusted to pH 34 with 1 M hydrochloric acid and concentrated. The residue is taken up on silica gel and purified by chromatography (mobile phase: cyclohexane/ethyl acetate 1:1, with 0.1% formic acid). 990 mg (1.77 mmol, 97% purity, 90% yield) of a solid are isolated.

Provenance & Evidence