Hydrochloric Acid → HCID 68534631, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl (2E)-3-(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoate (9) (2.20 g, 5.02 mmol) was dissolved in THF and EtOH (1:1, 50 mL). To this mixture was added 1 N NaOH (50 mL, excess) at room temperature and the stirred reaction heated to 70° C. for 0.5 h. After cooling to RT, the reaction mixture was acidified with 20% aqueous HCl, and then extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by flash column chromatography with CHCl3:MeOH (9:1 to 4:1) as an eluent to give 2.02 g (98%) of compound (10) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.70 (d, J=8.0 Hz, 1H), 7.64 (d, J=16.0 Hz, 1H), 7.57 (s, 1H), 7.26 (dd, J1=12.0 Hz, J2=12.0 Hz, 4H), 7.22 (d, J=4.0 Hz, 1H), 7.14 (d, J=1.8 Hz, 2H), 7.12 (s, 1H), 7.06 and 7.04 (dd, J=12.0 Hz, J2=6.8 Hz, 1H), 6.60 (d, J=8.0 Hz, 2H), 6.22 (d, J=16.0 Hz, 1H), 3.92 (s, 3H), 2.24 (s, 3H). LCMS (ESI) m/z 439.07 (M+H)+.

Provenance & Evidence