Lithium hydroxide, monohydrate → HCID 23579171, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the above ethyl ester (15) (140 mg, 0.52 mmol) in absolute EtOH (4 mL) was added LiOH—H2O (0.75 mL, 1.5 mmol, 2N solution in water). The reaction was heated at 50° C. for 1 h, then concentrated to remove excess EtOH. After acidification with 5% citric acid (20 mL), the product was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4) and concentrated to give a white solid (16) (110 mg, 88%). 1H NMR (400 MHz, CDCL3) δ 7.31 (dd, J=15.2, 10.8 Hz, 1H), 6.25 (dd, J=15.2, 10.8 Hz, 1H), 6.11 (quintet, J=7.2 Hz, 1H), 5.81 (d, J=15.2 Hz, 1H), 4.58 (br s, 1H), 3.24 (m, 2H), 2.37 (m, 2H), 1.44 (s, 9H); MS (ESI−) m/z 240.11 (M−H+).

Provenance & Evidence