tert-Butyl hydroperoxide → HCID 71279181, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-oxo-3-(pyridin-3-yl)propanoate (4 g, 22.3 mmol) in ethyl acetate (200 mL) were added at RT tetrabutylammonium iodide (1.65 g, 4.46 mmol), benzylamine (4.78 g, 4.87 mL, 44.6 mmol) and tert-butyl hydroperoxide (5.5M solution in decane, 16.2 mL, 89.3 mmol). The reaction mixture was stirred at 40° C. for 19 h. Sodium thiosulphate (10% aqueous solution, 200 mL) was added at RT and the reaction mixture was stirred for 10 min (until negative peroxide test). The aqueous phase was separated, the organic phase was washed with water (2×100 mL) and brine (20 mL). The aqueous phases were back-extracted with ethyl acetate (1×100 mL) and the combined organic phase was dried over MgSO4, filtered and evaporated to give 11.18 g of yellow semi-solid. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as yellow solid (1.33 g, 4.75 mmol, 21.3% yield).

Provenance & Evidence