Lithium hydroxide, monohydrate → HCID 18186385, compound

Participants

Reaction Steps

To a solution of ethyl (2E)-3-(4-{[2-(4-fluorophenyl)-6-hydroxy(1,2,3,4-tetrahydroisoquinolyl)]methyl}phenyl)prop-2-enoate (0.16 g, 0.37 mmol) in tetrahydrofuran (6 mL) was added a solution of lithium hydroxide monohydrate (0.20 g, 4.77 mmol) in water (3 mL). After it stirring at room temperature for 20 hours, the tetrahydrofuran was evaporated. The aqueous solution was neutralized with 5% aqueous HCl and extracted with dichloromethane. The extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 75-100% ethyl acetate/hexane) to provide the title compound (0.85 g, 57% yield): 1H NMR (CDCl3) 7.72 (d, 1H), 7.40 (d, 2H), 7.02 (d, 2H), 6.93 (m, 2H), 6.76 (m, 2H), 6.61 (m, 2H), 6.56 (dd, 1H), 6.42 (d, 1H), 4.75 (t, 1H), 3.55 (m, 1H), 3.46 (m, 1H), 3.16 (m, 1H), 2.87-3.00 (m, 2H), 2.64 (dt, 1H); ES-MS m/z 404 [M+H]+.

Provenance & Evidence