Potassium Hydroxide → HCID 18687828, compound

Participants

Reaction Steps

1.0 N Aqueous potassium hydroxide (8.0 mL, 8.0 mmol) was added to a stirred suspension of [11 -(4-methoxycarbonylmethoxy-phenyl)-benzo[b]naphtho[2,3-d ]thiophen-3-yloxy]-acetic acid methyl ester (0.750 g, 1.54 mmol) in THF (20 mL) and methanol (13 mL). Dissolution occurred. After 3 h at ambient temperature, the reaction mixture was diluted with water and extracted with ether (100 mL). The aqueous phase was acidified with 10% aqueous HCl and filtered. The solid was washed with water and triturated with pet. ether. The solid was dried in vacuo at 70° C. to provide a grey solid. This solid was recrystalized from acetic acid to provide the title compound as a white solid (0.502, 71%): mp 220-222° C.: NMR (DMSO-d6); δ12.8 (broad s, 2 H), 8.54 (s, 1 H), 8.02 (d, J=8 Hz, 1 H), 7.56-7.40 (m, 4 H), 7.31 (d, J=8 Hz, 2 H), 7.23 (d, J=8 Hz, 2 H), 6.73 (dd, J=9, 1 Hz, 1 H), 6.56 (d, J=9 Hz, 1 H), 4.85 (s, 2 H), 4.74 (s, 2 H), 1.97 (s, 2.49 H, 0.83 mol acetic acid); MS (FAB+): 459 (20%, M+H); Anal. Calc. for C26H18O6S.0.83CH3CO2 H: C, 65.46, H, 4.24, N, 0.00. Found: C, 64.47, H, 4.05, N, 0.03.

Provenance & Evidence