(E)-3-(3-chlorophenyl)prop-2-enal

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and (E)-3-(3-chlorophenyl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 13 as a white solid (62 mg, 46%). Analytical data for 13: 1H NMR (500 MHz, CDCl3) δ 9.41 (s, 1H), 7.88 (ddd, J=9.1, 6.0, 3.2 Hz, 1H), 7.40-7.29 (m, 3H), 7.31-7.22 (m, 2H), 7.10-7.02 (m, 2H), 7.02-6.93 (m, 4H), 4.09 (d, J=6.8 Hz, 1H), 3.58 (ddd, J=9.8, 6.9, 4.9 Hz, 1H), 3.31 (dd, J=14.9, 4.9 Hz, 1H), 2.42 (dd, J=14.9, 9.8 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 168.6, 159.1 (d, JCF=243.4 Hz), 155.4 (d, JCF=241.8 Hz), 148.9, 140.0, 136.8, 136.5, 134.4, 129.9, 129.3, 129.1, 128.5, 127.9, 127.3, 127.0, 118.3 (dd, JCF=12.6, 8.9 Hz), 117.1 (dd, JCF=25.6, 8.9 Hz), 116.6 (dd, JCF=24.8, 9.3 Hz), 114.5 (dd, JCF=26.8, 3.6 Hz), 110.7 (d, JCF=3.8 Hz), 47.0, 38.6, 32.6; IR (film) cm−1 1773, 1636, 1597, 1528, 1481, 1464, 1171, 1117, 1079, 813, 741; LRMS (ESI): Mass calcd for [M+H]+ C25H18ClF2N2O2: 451.1. found 451.3; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 5% IPA/3% MeOH/hexanes 0.5 mL/min, 280 nm), Rt1 (minor)=49.1, Rt2 (major)=70.2 min; er=>99:1. Prepared The unpurified residue was purified by flash chromatography