Ethanol → 3-[4-(6-Methoxy-3-methyl-2-thiophen-3-yl-naphthalen-1-yloxy)-phenyl]-acrylic acid

Participants

Reaction Conditions

Reaction Steps

A solution containing 3-[4-(6-Methoxy-3-methyl-2-thiophen-3-yl-naphthalen-1-yloxy)-phenyl]-acrylic acid ethyl ester (201) (0.27 g, 0.61 mmol), 1 N NaOH (5 mL), EtOH (4 mL), THF (4 mL) was heated at 60° C. for 2.5 h. Reaction mixture was cooled to room temperature and quenched with 20% HCl then extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified with 1.5% to 3.5% MeOH in DCM over 30 min to give 0.25 g (99%) of the title compound (202) as a white foam. 1H NMR (400 MHz, d-CDCl3): δ 2.31 (s, 3H), 3.92 (s, 3H), 6.24 (d, J=16 Hz, 1H), 6.64 (d, J=8.8 Hz, 2H), 6.90-6.92 (m, 1H), 7.02-7.05 (m, 2H), 7.12 (m, 1H), 7.21-7.23 (m, 1H), 7.31 (d, J=8.6 Hz, 2H), 7.56 (m, 1H), 7.64 (d, J=15.9 Hz, 1H), 7.71 (d, J=9.2 Hz, 1H).

Provenance & Evidence