Water → 4-Oxo-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-butyric acid methyl ester

Participants

Reaction Steps

To a solution of (Z)-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-hex-4-enoic acid methyl ester (3.83 g) obtained in Step 2 in a mixed solvent of dioxane (60 mL)-water (15 mL) was added 2,6-lutidine (2.8 mL). Then, to this was added dropwise a tert-butanol solution of osmium tetroxide (5 mg/mL, 12 mL) over 5 minutes, followed by stirring the reaction mixture at room temperature for 3 minutes. Then, to the reaction mixture was added dropwise-aqueous-sodium periodate solution (10.3 g/25 mL) over 7 minutes, followed by stirring the reaction mixture at room temperature for 2 hours. After addition of ethyl acetate to the reaction mixture, the organic layer was separated. The organic layer was washed successively with 1N aqueous hydrochloric acid solution, water, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium thiosulfate solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:4 to 1:3) to give 4-oxo-3-[4-(tetrahydropyran-2-yloxy)-phenyl]-butyric acid methyl ester (2.59 g).

Provenance & Evidence