tert-Butyl peroxybenzoate → HCID 67452919, compound

Participants

Reaction Conditions

Reaction Steps

Into a 10000-mL 3-necked round-bottom flask were placed methyl 2-cyclopropyl-4,5-dihydrooxazole-4-carboxylate (294 g, 1.74 mol, 1.00 equiv.), CuBr (274 g, 1.92 mol, 1.10 equiv.) and toluene (3000 mL). This was followed by the addition of tert-butyl perbenzoate (506 g, 2.61 mol, 1.50 equiv.) dropwise with stirring at 60° C. over 60 minutes. The resulting solution was stirred overnight at 80° C. in an oil bath. The reaction mixture was cooled to room temperature, then quenched by the addition of 2000 mL of 10% NH4OH. The resulting solution was extracted with 3×2000 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:20). This resulted in 200 g (69% yield) of methyl 2-cyclopropyloxazole-4-carboxylate as a yellow oil.

Provenance & Evidence