反应详情

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and (E)-3-(4-methoxyphenyl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 9 as an off-white solid (102 mg, 76%). Analytical data for 9: 1H NMR (500 MHz, CDCl3) δ 9.38 (d, J=8.1 Hz, 1H), 7.89 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.39-7.29 (m, 3H), 7.10-6.93 (m, 6H), 6.88-6.83 (m, 2H), 4.09 (d, J=6.8 Hz, 1H), 3.81 (s, 3H), 3.55 (ddd, J=10.1, 6.8, 4.6 Hz, 1H), 3.29 (dd, J=14.9, 4.6 Hz, 1H), 2.38 (dd, J=14.9, 10.1 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 169.0, 159.1 (d, JCF=243.6 Hz), 158.4, 155.4 (d, JCF=241.1 Hz), 148.9, 137.1, 136.3, 130.0, 129.7, 129.2, 128.3, 128.0, 118.4 (dd, JCF=12.3, 9.5 Hz), 117.1 (dd, JCF=25.7, 8.7 Hz), 116.5 (dd, JCF=24.7, 9.5 Hz), 114.0, 114.5 (dd, JCF=26.8, 3.7 Hz), 111.0 (d, JCF=3.8 Hz), 55.3, 47.5, 38.3, 31.8; IR (film) cm−1 1772, 1617, 1528, 1513, 1481, 1464 1249, 1176, 1118, 1100, 1033, 766, 735, 700; LRMS (ESI): Mass calcd for [M+H]+ C26H21F2N2O3: 447.1. found 447.4; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 5% IPA/3% MeOH/hexanes 0.5 mL/min, 280 nm), Rt1 (major)=48.1, Rt2 (minor)=56.9 min; er=99:1.

1. customPrepared
2. customThe unpurified residue was purified by flash chromatography