Diethyl Oxalate → HCID 124026306, compound

Participants

Reaction Steps

To a solution of 1-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)ethanone (27 g, 71 mmol) in anhydrous tetrahydrofuran (300 mL) was added lithium bis(trimethylsilyl)amide (106 mL, 106 mmol, 1 M in tetrahydrofuran) slowly at −78° C. under nitrogen. After 0.5 h, diethyl oxalate (15.63 g, 107.0 mmol) was added, and the reaction mixture was warmed to room temperature. After 6 h, the reaction mixture was quenched with 3 M aqueous hydrochloric acid until the solution reached pH ˜3. The mixture was extracted with ethyl acetate (2×200 mL). The combined organics were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated to provided ethyl 4-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-2,4-dioxobutanoate as an orange solid (40 g), which was used without further purification. LCMS: [M+H]+ 479.0, [M+Na]+ 501.0, [M+Na+CH3CN]+ 542.0.

Provenance & Evidence