Lithium Hydroxide → HCID 25022352, compound

Participants

Reaction Steps

To a stirred solution of 4.2 (0.052 g, 0.11 mmol) in THF (2.00 mL) and EtOH (2.00 mL) at 23° C. was added 1N lithium hydroxide (2.00 mL, 2.00 mmol). Stirring continued for 16 hours. The reaction mixture was concentrated in vacuo, 1N HCl was added to reach pH 1, and the resulting mixture was extracted with EtOAc (3×10 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes) to give compound 4 as a clear oil (0.0466 g, 92% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.58 (1H, d, J=8.2 Hz), 7.41 (1H, dd, J=8.2, 2.0 Hz), 7.30 (2H, d, J=8.6 Hz), 7.08 (1H, d, J=2.0 Hz), 7.00 (1H, t, J=8.8 Hz), 6.93 (2H, d, J=8.6 Hz), 6.86 (1H, m), 6.80 (1H, dd, J=5.9, 3.3 Hz), 5.00 (2H, s), 4.06 (1H, m), 3.80 (3H, s), 2.81 (1H, dd, J=15.6, 8.4 Hz), 2.72 (1H, dd, J=15.6, 6.6 Hz), 1.84 (3H, d, J=2.3 Hz), 1.24 (9H, s). MS ESI (neg.) m/e: 947.3 (2M−H)+, 473.2 (M−H)+.

Provenance & Evidence