Sodium hydride → (E)-5-(4-hydroxy-3-methoxyphenyl)-1-(4-iodophenyl)-pent-4-ene-1,3-dione

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Reaction Steps

By a similar procedure as described in Example 1 using 1-(4-iodophenyl)-butane-1,3-dione (prepared by reaction of 4-iodoacetophenone with ethyl acetate in the presence of sodium hydride) in place of 5,5-dimethylhexane-2,4-dione, (E)-5-(4-hydroxy-3-methoxyphenyl)-1-(4-iodophenyl)-pent-4-ene-1,3-dione (0.40 g, 0.95 mmol, 31%) was obtained as a yellow solid: mp 139-141° C.; 1H NMR (400 MHz; CDCl3) δ 3.95 (3H, s, OCH3), 5.87 (1H, s, OH), 6.27 (1H, s, H-2), 6.42 (1H, d, J=16.0 Hz, H-4), 6.87 (1H, d, J=8.4 Hz, H-5′), 6.99 (1H, s, H-2′), 7.06 (1H, d, J=8.4 Hz, H-6′), 7.54-7.60 (3H, m, H-5, H-3″, H-5″), 7.41-7.62 (2H, m, H-2″, H-6″), 16.18 (1H, s, OH) ppm; 13C NMR (100 MHz; CDCl3) δ 187.5, 180.8, 148.1, 146.9, 140.9, 138.0, 135.5, 128.9, 127.6, 123.2, 120.9, 115.1, 109.6, 100.0, 97.1, 56.0 ppm.

Provenance & Evidence