Methyl 7-(6,7-dimethyl-5-hydroxyindan-4-yl)-7-(4-fluorophenyl)heptanoate → 7-(6,7-Dimethyl-5-hydroxy-1-oxoindan-4-yl)-7-(4-fluorophenyl)heptanoic acid

Participants

Reaction Steps

To a solution of methyl 7-(6,7-dimethyl-5-hydroxyindan-4-yl)-7-(4-fluorophenyl)heptanoate (1.4 g) in benzene (40 ml) was added a mixture of pyridinium chlorochromate (3.8 g) and cerite (7 g) and the mixture was stirred for 2 hours. The reaction mixture was filtered and the filtrate was washed with water and saturated saline and dried with magnesium sulfate. Tetrahydrofuran (10 ml) and 1N sodium hydroxide (10 ml) were added to the residue and the mixture was stirred at room temperature for 13 hours. The solvent was distilled off under reduced pressure and the residue was acidified with 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 recrystallized from acetonitrile to obtain 7-(6,7-dimethyl-5-hydroxy-1-oxoindan-4-yl)-7-(4-fluorophenyl)heptanoic acid (0.4 g) (Compound 37). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Provenance & Evidence