Lithium hydroxide, monohydrate → HCID 25210999, compound

Participants

Reaction Steps

A solution of 5-(5-Difluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid ethyl ester (Preparative Example 25, 1.0 g, 3.48 mmol) in THF (20 mL) was treated with an aqueous solution (5 mL) of lithium hydroxide monohydrate (292 mg, 6.96 mmol) and allowed to stir for 20 hr. The reaction was then evaporated to a small volume and treated with a 1 N aqueous hydrochloric acid solution to a pH of −2 and the resulting solids filtered, washed with water and air dried to afford product as a colorless solid (900 mg, 99%). 1H NMR (DMSO-d6) 2.29 (s, 3 H), 7.44 (t, J=51.9, 1 H), 7.66 (d, J=2.6, 1 H), 7.78 (d, J=2.6, 1 H). 13C NMR 7.7, 108.1 (t, J=236), 115.0, 130.3, 134.3, 134.5, 137.4, 157.8, 159.6 (t, J=26), 163.1. 19F NMR −118.8 (J=51.5). LC/MS 5.41 min, [M+1]+ 260.

Provenance & Evidence