Water → (Z)-7-(4-fluorophenyl)-7-(2-hydroxy-5-hydroxyiminomethyl-3,4,6-trimethylphenyl)heptanoic acid

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Reaction Steps

To a solution 7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid (1.3 g) in ethanol (13 ml) were added sodium acetate (1.3 g), hydroxylamine hydrochloride (0.26 g) and water (2.6 ml) and the mixture was refluxed for 4 hours. The solvent was distilled off under reduced pressure. To the residue were added water and 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to obtain (Z)-7-(4-fluorophenyl)-7-(2-hydroxy-5-hydroxyiminomethyl-3,4,6-trimethylphenyl)heptanoic acid (0.55 g) and (E)-7-(4-fluorophenyl)-7-(2-hydroxy-5-hydroxyiminomethyl-3,4,6-trimethylphenyl)heptanoic acid (0.75 g) (Compounds 47 and 48). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Provenance & Evidence