Diethyl Malonate → Diethyl 2-((1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl)malonate

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Reaction Steps

Sodium (5 mg, 0.215 mmol) was dissolved in EtOH (2 mL) to form a solution of NaOEt and then diethyl malonate (0.033 mL, 0.215 mmol) was added. The reaction mixture was stirred at rt for 30 min and (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate (10 mg, 0.022 mmol) was then added. The reaction was stirred at 120° C. under microwave conditions for 30 min. Catalytic amount of n-Bu4NI was added and the reaction was stirred at 120° C. under microwave conditions for 18 h. The reaction was added sat′d aq NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude oil was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes) to afford the title compound (8 mg, 82% yield) as a clear oil. LCMS, [M-Et+H]+=425.4.

Provenance & Evidence