HCID 59014506, compound → HCID 11517219, compound

Participants

Reaction Steps

A 1:1 EtOAc/EtOH solution (4 mL) of (2E)-3-(4-{[6-hydroxy-2-(3-hydroxyphenyl)-3-methyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid (251) (0.041 g, 0.01 mmol, 1 equiv) was treated with 5% Pd—C (0.027 g, 0.02 mmol, 0.1 equiv) and the reaction vessel was equipped with an H2-filled balloon. After 14 h at ambient temperature, the crude mixture was filtered through a pad of Celite. Concentration gave a light pink solid that was purified by radial chromatography (SiO2, 1 mm plate, 90:10; CHCl3/MeOH) to afford the title compound (252) as a pink solid (0.018 g, 44%). 1H NMR (CD3OD, 400 MHz) δ 7.58 (d, J=9.0 Hz, 1H), 7.40 (s, 1H), 7.07-7.03 (m, 2H), 6.95-6.89 (m, 3H), 6.62 (dd, J=8.1, 2.3 Hz, 1H), 6.55-6.52 (m, 2H), 6.43 (d, J=8.5 Hz, 2H), 2.75 (t, J=7.7 Hz, 2H), 2.34 (t, J=7.3 Hz, 2H), 2.17 (s, 3H).

Provenance & Evidence