Hydrochloric Acid → HCID 68534800, compound

Participants

Reaction Steps

A THF solution (2 mL) of ethyl (2E)-3-[4-({3-methyl-6-(methyloxy)-2-[3-(methyloxy)phenyl]-1-naphthalenyl}oxy)phenyl]-2-propenoate (249) (0.030 g, 0.06 mmol, 1 equiv) was treated with 1 M aqueous LiOH (0.260 mL). After 2 h at 50° C., the mixture was acidified with 3M aqueous HCl to pH ca. 1 and extracted with EtOAc (3×5 mL). The pooled organic portions were dried (Na2SO4) and concentrated. Radial chromatography (SiO2, 1 mm plate, 80:20; hexanes/EtOAc) afforded the title compound (250) as a white foam (0.024 g, 85%). 1H NMR (CDCl3, 400 MHz) δ 7.69 (d, J=9.2 Hz, 1H), 7.63 (d, J=15.9 Hz, 1H), 7.55 (s, 1H), 7.27 (d, J=8.3 Hz, 2H), 7.16 (dd, J=7.9, 7.9 Hz, 1H), 7.13 (d, J=2.0 Hz, 1H), 7.03 (dd, J=9.1, 2.2 Hz, 1H), 6.77 (dd, J=8.1, 1.9 Hz, 1H), 6.71 (d, J=7.4 Hz, 1H), 6.64-6.60 (m, 3H), 6.22 (d, J=15.9 Hz, 1H), 3.92 (s, 3H), 3.62 (s, 3H), 2.25 (s, 3H). TLC (98:2; CHCl3/MeOH): Rf=0.05.

Provenance & Evidence