Potassium Hydroxide → HCID 10159240, compound

Participants

Reaction Steps

To a stirred solution of {[6-(3-benzoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetic acid methyl ester (0.128 g, 0.293 mmol) in THF:MeOH (3:2, 10 mL) at 0° C. was added 1 N KOH (0.879 mL, 0.879 mmol) dropwise. The reaction was stirred at this temperature for 0.25 h and then warmed to room temperature for 1 h. After concentration, the residue was diluted with H2O, and this mixture was acidified to pH 1 with 2 N HCl. After stirring at room temperature for 3 h, the solid was filtered and washed with excess H2O and hexane. At this point, the compound was dried under high vacuum to afford the product (0.116 g) as a yellow solid, mp 178-181° C. Mass spectrum (−APCl, [M−H]−) m/z 421. 1HNMR (500 MHz, DMSO-d6): δ11.05-14.15 (br s, 1H), 8.17 (d, J=1.5 Hz, 1H), 7.84 (d, J=9.0 Hz, 1H), 7.76-7.81 (m, 3H), 7.70 (d, J=8.8 Hz, 1H), 7.52-7.57 (m, 2H), 7.42-7.51 (m, 2H), 7.31-7.37 (m, 3H), 7.18-7.24 (m, 2H), and 4.77 ppm (s, 2H). Elemental Analysis for C27H18O5.0.5H2O: Calculated: C, 75.17; H, 4.44; N, 0.00 Found: C, 75.03; H, 4.34; N, 0.14

Provenance & Evidence