Lithium hydroxide, monohydrate → HCID 22137609, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the above ethyl ester (22) (2.60 g, 8.4 mmol) in absolute EtOH (30 mL) was added LiOH—H2O (720 mg, 17 mmol, in 10 mL of water). The reaction was heated to 50° C. for 1 h, then concentrated to remove excess EtOH. After acidification with 5% citric acid (50 mL), the product was extracted with EtOAc (2×100 mL). The combined organic extracts were washed with brine (100 mL), dried (MgSO4) and concentrated to give a white solid (23) (2.32 g, 98%). 1H NMR (500 MHz, CDCL3) δ 7.31 (dd, J=15.5, 11.0 Hz, 1H), 6.18 (dd, J=15.5, 11.0 Hz, 1H), 6.08 (dd, J=15.5, 7.0 Hz, 1H), 5.80 (d, J=15.5 Hz, 1H), 4.10 (m, 2H), 2.75 (m, 2H), 2.25 (m, 1H), 1.70 (m, 2H) 1.44 (s, 9H), 1.33 (m, 2H); MS (ESI−) m/z 280.74 (M−H+).

Provenance & Evidence