반응 #168242

반응 방정식

3-amino-3-(4-phenoxyphenyl)acrylonitrile

methyl 4-(3-methoxy-3-oxopropanoyl)benzoate

ammonium chloride

→

methyl 4-(5-cyano-4-oxo-6-(4-phenoxyphenyl)-1,4-dihydropyridin-2-yl)benzoate

수율 65.0%

반응 조건

후처리

1. 1
   기타was microwaved at 230° C. for 20 min
2. 2
   추출extracted with ethyl acetate (80 mL)
3. 3
   세척The ethyl acetate phase was washed with saturated ammonium chloride (10 mL), water (10 mL), brine (5 mL)
4. 4
   건조dried (MgSO4)
5. 5
   농축concentrated
6. 6
   세척Silica gel chromatography, eluting with 0-80% ethyl acetate in hexanes
7. 7
   기타gave impure products
8. 8
   기타The material was triturated with dichloromethane
9. 9
   여과The white solid was collected by filtration

실험 절차

A mixture of 3-amino-3-(4-phenoxyphenyl)acrylonitrile (0.517 g, 2.188 mmol) and methyl 4-(3-methoxy-3-oxopropanoyl)benzoate (2.068 g, 8.75 mmol) was microwaved at 230° C. for 20 min. After cooling to room temperature, the mixture was poured into saturated ammonium chloride (25 mL) and extracted with ethyl acetate (80 mL). The ethyl acetate phase was washed with saturated ammonium chloride (10 mL), water (10 mL), brine (5 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0-80% ethyl acetate in hexanes, gave impure products. The material was triturated with dichloromethane. The white solid was collected by filtration to give methyl 4-(5-cyano-4-oxo-6-(4-phenoxyphenyl)-1,4-dihydropyridin-2-yl)benzoate (0.598 g, 65% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.25 (1H, br. s), 8.17 (2H, br. s), 8.02 (1H, br. s), 7.71 (2H, br. s), 7.40 (2H, t, J=7.91 Hz), 7.24 (1H, br. s), 7.03-7.16 (4H, m), 6.62 (1H, br. s), 3.95 (3H, s); MS (ES+) m/z: 423 (M−H); LC retention time: 4.118 min (analytical HPLC Method A).

출처