Hydrogen Peroxide → HCID 25056011, compound

Participants

Reaction Steps

To a stirred solution of 6.6 (0.0282 g, 0.043 mmol) in THF (3.00 mL, 37 mmol) and water (1.00 mL, 56 mmol) at 0° C. was added 35% hydrogen peroxide (0.025 mL, 0.26 mmol) followed by lithium hydroxide (0.0020 g, 0.085 mmol). Stirring continued for 1 hour and 40 minutes. A saturated solution of Na2SO3 was added, and stirring was continued at 0° C. for 30 minutes. The mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-30% EtOAc/hexane) to give compound 6 as a clear oil (0.0103 g, 48% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.28 (1H, d, J=1.6 Hz), 7.58 (1H, d, J=8.6 Hz), 7.40 (1H, dd, J=8.2, 2.0 Hz), 7.17 (2H, d, J=8.8 Hz), 6.86 (1H, dt, J=8.0, 3.9 Hz), 6.78 (1H, dd, J=5.9, 3.1 Hz), 6.07 (1H, d, J=1.6 Hz), 4.99 (2H, s), 4.54 (1H, dd, J=7.9, 7.4 Hz), 3.79 (3H, s), 3.35 (1H, dd, J=16.6, 7.9 Hz), 2.98 (1H, dd, J=16.4, 7.4 Hz), 1.23 (9H, s). MS ESI (neg.) m/e: 502.1 (M−H)+.

Provenance & Evidence