Acetic Acid → Ethyl 3-phenyl-2-(thiophene-2-carbonyl)acrylate

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[O:1]=[C:2]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].N1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[C:20](O)(=O)[CH3:21]>C1C=CC=CC=1>[C:20]1([CH:21]=[C:3]([C:2]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[O:1])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

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실험 절차

A solution of ethyl 3-oxo-3-(thiophen-2-yl)propanoate (4.10 g, 20.7 mmol), benaldehyde (2.32 ml, 22.8 mmol), piperidine (0.205 ml, 2.07 mmol) and acetic acid (0.593 ml, 10.4 mmol) in benzene (80 ml) was heated at 85° C. for 5 hours using a Dean-Stark trap for removal of the water formed. The reaction solution was concentrated. The resulting residue was purified via flash chromatography (silica gel cartridge with eluent of 0-5% ethyl acetate/hexane) to give ethyl 3-phenyl-2-(thiophene-2-carbonyl)acrylate as a white solid (5.563 g, 94% yield). LCMS m/z 309.1 (M+23); HPLC: Rt 3.15 min.