2,2-Dimethyl-5-(3-(trifluoromethyl)benzyl)-1,3-dioxane-4,6-dione → 2-(3-(Trifluoromethyl)benzyl)malonic acid

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Reaction Steps

A solution of 2,2-dimethyl-5-(3-(trifluoromethyl)benzyl)-1,3-dioxane-4,6-dione (4.0 g, 13.23 mmol, Intermediate 15: step a) in 40% aqueous NaOH (20 mL) was heated in a 93° C. oil bath for 48 hours. The mixture was then cooled to room temperature and extracted with EtOAc. The aqueous layer was acidified to pH 2 with 6 N aqueous HCl then extracted with EtOAc (2×). The combined EtOAc extracts were washed with H2O followed by brine and dried over Na2SO4. The mixture was filtered, solvent was removed under reduced pressure and crude product purified by chromatography (10% MeOH/0.2% HOAc mixture in DCM) to afford the title compound as an off-white solid.

Provenance & Evidence