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

Participants

Reaction Conditions

Reaction Steps

ethyl 4-[(4-{[3-methyl-6-(methyloxy)-2-phenyl-1 naphthalenyl]oxy}phenyl)oxy]butanoate (288) (0.300 g, 0.638 mmol) was dissolved in a 1:1 THF:EtOH (1:1, 30 mL) mixture. To the above mixture was added 1 N NaOH (6.4 mL) at room temperature and heated to 70° C. The reaction mixture was kept at that temperature for 2 h and cooled at RT. Reaction mixture was concentrated under reduced pressure to afford the residue and the residue was acidified with 25% aqueous HCl (30 mL), and then extracted with EtOAc (3×50 mL). The combined organic layer was washed with brine (1×30 mL), dried (Na2SO4), and concentrated under reduced pressure to afford the crude product which was purified by flash SiO2 column chromatography using hexanes:EtOAc (19:1 to 1:1) as an eluent to afford 0.247 g (88%) of the title product (289) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.10 (s, 1H), 7.65 (s, 1H), 7.57 (d, J=9.2 Hz, 1H), 7.30 (d, J=2.4 Hz, 1H), 7.29 (d, J=7.6 Hz, 2H), 7.24 (m, 1H), 7.16 (d, J=8.4 Hz, 2H), 7.05 and 7.03 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.66 (d, J=9.2 Hz, 2H), 6.47 (d, J=9.2 Hz, 2H), 3.85 (s, 3H), 3.79 (t, J=6.4 Hz, 2H), 2.30 (t, J=7.2 Hz, 2H), 2.16 (s, 3H), 1.83 (quintet, J=6.8 Hz, 2H). LCMS (ESI) m/z 443.18 (M+H)+.

Provenance & Evidence