Reaction Steps
Prepared in 53% yield (54.4 mg, 0.16 mmol) from the reaction of 2-choro-2-(4-chlorophenyl)-N-(phenylmethoxy)acetamide (95.5 mg, 0.31 mmol) with furan via general procedure B. Rf=0.48 (3:1, hexanes:EtOAc); 1H-NMR (500 MHz, CDCl3): δ 7.50-7.44 (m, 2H), 7.44-7.34 (m, 3H), 7.28 (ABd, J=8.5 Hz, 2H), 7.05 (ABd, J=8.5 Hz, 2H), 6.55 (dd, J=6.0, 1.1 Hz, 1H), 6.19 (dd, J=6.0, 1.7 Hz, 1H), 5.36 (d, J=1.3 Hz, 1H), 5.05 (d, J=11.0 Hz, 1H), 4.96 (d, J=11.0 Hz, 1H), 4.94 (dd, J=5.3, 1.8 Hz, 1H), and 4.38 (d, J=5.3 Hz, 1H); 13C-NMR (126 MHz, CDCl3): δ 169.7, 136.0, 136.0, 135.6, 133.8, 133.8, 132.0, 131.1, 129.83, 129.1, 128.8, 128.7, 91.8, 91.8, 83.1, 83.1, 78.3, and 56.5; IR (film) 3089, 3064, 3031, 2924, 1688, 1492, 1454, 1368, 1275, 1260, 1211, 1091, 1059, 1017 cm-1. HR-ESIMS: calculated for C19H17ClNO3 (M+H)+ 342.0891, observed 342.0886.
