[CH:1]([C:3]1[N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:16])[CH:5]=[CH:6][CH:7]=1)=O.[C:17]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:18]C([O-])=O.[K+].CC(O)=O.N1CCCCC1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:4]2[CH:5]=[CH:6][CH:7]=[C:3]2[CH:1]=[CH:18][C:17]([O:23][CH2:24][CH3:25])=[O:22])=[C:9]([CH3:16])[CH:10]=1)#[N:13]
To a mixture of 4-(2-formyl-1H-pyrrol-1-yl)-3-methylbenzonitrile (24.5 g, 116.7 mmol), DMAP (2.9 g, 23.3 mmol) and potassium monoethyl malonate (99.2 g, 583.3 mmol) in DMF (600 mL) was added AcOH (35.0 g, 583.3 mmol) and piperidine (29.8 g, 350 mmol). The resultant mixture was heated to 80° C. and stirred for 48 h. The reaction mixture was poured into cooled water and extracted with ethyl acetate (800 mL×3). The combined organic layers were washed with sat. NaHCO3 and brine, dried over Na2SO4, concentrated and purified by silica gel column chromatography (PE:EA=5:1) to afford ethyl 3-(1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)acrylate as a yellow oil (21.8 g, 67%).
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