Potassium Hydroxide → HCID 10185030, compound

Participants

Reaction Steps

Following the procedure described in Step 4 of Example 6, ethyl 2-({1-bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthyl}oxy)acetate (0.180 g, 0.345 mmol) was hydrolyzed with potassium hydroxide (0.077 g, 1.4 mmol) in THF (5 mL) and water (5 mL). Crystallization from acetonitrile and drying for 12 hours at 80° C. yielded 2-({1-bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthyl}oxy)acetic acid as a cream-colored solid (0.0807 g), mp 155-156° C. Mass spectrum (−ESI, [M−H]−) m/z 491; 1HNMR (500 MHz, DMSO-d6): δ13.0-13.5 (br s, 1H), 8.35 (d, 1H, J=1.2 Hz), 8.25 (d, 1H, J=8.9 Hz), 8.10 (d, 1H, J=9.0 Hz), 8.05 (dd, 1H, J=9.0 Hz and 1.7 Hz), 7.7 (d, 1H, J=7.8 Hz), 7.6 (d, 1H, J=7.9 Hz), 7.45 (d, 1H, J=9.2 Hz), 7.35-7.4 (m, 1H), 7.30-7.35 (m, 1H), 5.0 (s, 2H), 3.0 (t, 2H, J=7.9 Hz), 1.8-1.9 (m, 1H), 1.7-1.8 (m, 4H), 1.5-1.6 (m, 2H), 1.4-1.5 (m, 2H), and 1.15-1.25 ppm (m, 2H). Elemental Analysis for C27H25BrO4: Calculated: C, 65.13; H, 5.16; N, 0.00. Found: C, 64.83; H, 4.94; N, 0.06.

Provenance & Evidence