tert-Butyl peroxybenzoate → HCID 67452919, compound

Temperature

60 °C

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.

1. customInto a 10000-mL 3-necked round-bottom flask were placed
2. stirringThe resulting solution was stirred overnight at 80° C. in an oil bath
3. temperatureThe reaction mixture was cooled to room temperature
4. customquenched by the addition of 2000 mL of 10% NH4OH
5. extractionThe resulting solution was extracted with 3×2000 mL of ethyl acetate
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum
8. washeluted with ethyl acetate/petroleum ether (1:20)

ORD record

ord-2f68144d54e846d19ae2219f4529c573

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073879B2