Hydrochloric Acid → (2E)-3-(4-{[3-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl (2E)-3-(4-{[3-ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoate (59) (0.67 g, 1.49 mmol) in THF (10 mL) and EtOH (10 mL) was added 1 N NaOH (12 mL). The resulting mixture was heated at 60° C. for 2 h. Cooled in an ice bath, the mixture was acidified with 2 N HCl and extracted with EtOAc (3×50 mL). The extracts were combined and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product, which was triturated with hot hexanes (containing a small amount of CHCl3 and MeOH) to give 0.62 g (98%) of the title compound (60) as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.13 (t, J=7.5 Hz, 3H), 2.56 (q, J=7.5 Hz, 2H), 3.94 (s, 3H), 6.23 (d, J=15.9 Hz, 1H), 6.59 (d, J=8.8 Hz, 2H), 7.04 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.10-7.16 (m, 2H), 7.19 (d, J=2.5 Hz, 1H), 7.20-7.30 (m, 5H), 7.60 (s, 1H), 7.63 (d, J=15.8 Hz, 1H), 7.70 (d, J=9.2 Hz, 1H). LCMS (ESI): m/z 423 (M−H)−.

Provenance & Evidence