[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1)#[N:4].[CH:18](OCC)=[O:19].C(O)(=O)C>COCCOC.CC(=O)OCC>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH:18]=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1)#[N:4]
To a suspension of NaH (1.102 g, 27.6 mmol) in DME (15 mL) was added dropwise a solution of ethyl 3-(4-cyanophenyl)propanoate (1.4 g, 6.89 mmol) and ethyl formate (2.77 mL, 34.4 mmol) in DME (15 mL). The reaction mixture was then stirred at room temperature overnight. It was neutralized with acetic acid (1.7 mL), then extracted with EtOAc. The organic phases were collected, washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by a flash column chromatography, eluting with PE:EA=2:1, to give the title compound as a pale yellow oil (1.3 g, 82% yield). LCMS: rt=2.47 and 3.13 min (a mixture of ketone and enol isomer), [M+H+]=232.2
Loading…
