反应详情

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and trans-cinnamaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 5j as a white solid (91 mg, 73%). Analytical data for 5j: 1H NMR (500 MHz, CDCl3) δ 9.41 (br s, 1H), 7.91 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.40-7.32 (m, 5H), 7.31-7.27 (m, 1H), 7.14-7.10 (m, 2H), 7.10-7.05 (m, 1H), 7.04-6.96 (m, 3H), 4.11 (d, J=6.8 Hz, 1H), 3.64 (ddd, J=10.2, 6.8, 4.6 Hz, 1H), 3.39 (dd, J=14.9, 4.5 Hz, 1H), 2.46 (dd, J=14.9, 10.2 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 168.9, 159.1 (d, JCF=243.1 Hz), 155.4 (d, JCF=241.8 Hz), 148.9, 137.9, 137.0, 136.3, 129.2, 129.0, 128.6, 128.3, 128.0, 126.8, 118.4 (dd, JCF=12.5, 9.1 Hz), 117.1 (dd, JCF=25.7, 8.7 Hz), 116.6 (dd, JCF=24.8, 9.4 Hz), 114.5 (dd, JCF=27.0, 3.9 Hz), 111.0 (d, JCF=3.8 Hz), 47.3, 38.4, 32.7; IR (film) cm−1 1773, 1636, 1618, 1529, 1481, 1463, 1453, 1240, 1172, 1117, 1070, 766, 731; LRMS (ESI): Mass calcd for [M+H]+ C25H19F2N2O2: 417.1. found 417.4; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 20% IPA/hexanes; 1.0 mL/min, 280 nm), Rt1 (minor)=11.3, Rt2 (major)=17.8 min; er=98:2.

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