Lithium Hydroxide → HCID 86707793, compound

Participants

Reaction Steps

To a stirred solution of 3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid ethyl ester (non-polar compound from Preparation 5, 2 g, 3.72 mmol) in EtOH:H2O (1:1, 140 mL) was added lithium hydroxide (0.782 g, 18.62 mmol) at 0° C. Resulting reaction mixture was stirred at room temperature for 16 hours. After consumption of starting material, reaction mixture was concentrated in vacuo; suspension was diluted with water (100 mL) and Acidified with 1M HCl up to pH=2 at 0° C. Solid was precipitated out, which was filtered on Whatmann filter paper. Solid was dissolved in EtOAc (100 mL), dried over sodium sulphate, filtered and evaporated to afford solid. Solid was washed with n-pentane (3×5 mL), dried to afford white solid (1.6 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ: 2.75 (d, J=8.72 Hz, 2H), 2.81 (d, J=8.68 Hz, 2H), 3.37-3.39 (m, 1H), 4.29-4.41 (m, 2H), 7.55 (d, J=8.12 Hz, 2H), 7.77 (d, J=8.12 Hz, 2H), 7.84 (s, 2H), 12.50 (bs, 1H); LC-MS (m/z): 507.80 (M−H).

Provenance & Evidence