反应详情

温度

80 °C

Ethyl-2,4-dioxovalerate (0.555 g, 3.5 mmol) and 4-methoxyphenylhydrazine hydrochloride (0.67 g, 3.8 mmol) were mixed in ethanol and heated to 80° C. overnight. The reaction was cooled, diluted with water and extracted with EtOAc. Organic layers were combined and washed with water, 10% HCl, sat. NaHCO3, dried over MgSO4 and concentrated under reduced pressure. The residue was purified on silica gel (20% EtOAc in hexanes to 30% EtOAc in hexanes). Two regioisomers were isolated, the title regioisomer being the more polar (yield 492 mg). LC-MS (C14H16N2O3 calculated 260) m/z 261 (M+H).

1. temperatureThe reaction was cooled
2. extractionextracted with EtOAc
3. washwashed with water, 10% HCl, sat. NaHCO3
4. dry with materialdried over MgSO4
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified on silica gel (20% EtOAc in hexanes to 30% EtOAc in hexanes)
7. customTwo regioisomers were isolated