Hydrochloric Acid → HCID 59014506, compound

Participants

Reaction Steps

To a solution of (2E)-3-[4-({3-methyl-6-(methyloxy)-2-[3-(methyloxy)phenyl]-1-naphthalenyl}oxy)phenyl]-2-propenoic acid (250) (0.032 g, 0.07 mmol, 1 equiv) in CH2Cl2 (3 mL) at 0° C. was added boron tribromide (0.66 mL, 1.0 M, 9.0 equiv). After 2.5 h, the mixture was treated with saturated aqueous NaHCO3, reacidified to a pH of 2 with 1 M HCl, and extracted with EtOAc (3×5 mL). The pooled organic portions were dried (MgSO4) and concentrated. Radial chromatography (SiO2, 1 mm plate, 70:30; CHCl3/MeOH) furnished the title compound (251) as a pale yellow foam (0.017 g, 57%). 1H NMR (CD3OD, 400 MHz) δ 7.59 (d, J=9.0 Hz, 1H), 7.48 (s, 1H), 7.44-7.36 (m, 1H), 7.29 (d, J=8.2 Hz, 2H), 7.10 (d, J=2.2 Hz, 1H), 7.04 (dd, J=7.5, 7.5 Hz, 1H), 6.94 (dd, J=9.0, 2.2 Hz, 1H), 6.64-6.62 (m, 1H), 6.57-6.55 (m, 4H), 6.39-6.24 (m, 1H), 2.20 (s, 3H). TLC (90:10; CHCl3/MeOH): Rf=0.54.

Provenance & Evidence