Ethanol → HCID 57672379, compound

Participants

Reaction Steps

To a stirred solution of 8.1 (0.0529 g, 0.11 mmol) in THF (2.00 mL, 24 mmol) and EtOH (2.00 mL, 34 mmol) at 23° C. was added 1N sodium hydroxide (2.00 mL, 2.0 mmol). Stirring continued for 17 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 then purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes) to give compound 8 as a clear oil (0.0382 g, 74% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.58 (1H, d, J=8.2 Hz), 7.40 (1H, dd, J=8.2, 2.0 Hz), 7.16 (2H, d, J=9.0 Hz), 7.08 (1H, d, J=2.0 Hz), 7.00 (1H, t, J=8.8 Hz), 6.92 (2H, d, J=9.0 Hz), 6.87 (1H, dt, J=8.9, 3.9 Hz), 6.80 (1H, m), 5.58-5.49 (2H, m), 4.99 (2H, s), 4.14 (1H, m), 3.79 (3H, s), 2.75 (1H, dd, J=15.1, 6.8 Hz), 2.64 (1H, dd, J=15.1, 8.6 Hz), 1.66 (3H, d, J=5.1 Hz), 1.23 (9H, s). m/e: 951.4 (2M−H)+, 475.1 (M−H)+.

Provenance & Evidence