Water → HCID 59479418, compound

Participants

Reaction Steps

To 65E (0.45 g, 1.15 mmol) in EtOH (8 mL) at 0° C. was added Oxone® (0.99 g, 1.6 mmol, 1.4 eq.) in water (8 mL). The mixture was stirred from 0° C. to rt over 18 h. It was quenched with sat. NaHCO3 and Na2S2O3. The precipitate was removed by filtration and the filtrate was condensed, diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4. After removal of solvent, the crude was purified by silica column chromatography using gradient EtOAc in hexanes to give 65J (0.44 g, 81% yield). 1H NMR (400 MHz, 90° C., DMSO-d6) δ ppm 0.88 (t, J=7.15 Hz, 3H) 1.13-1.17 (m, 3H) 1.19-1.27 (m, 9H) 1.34 (d, J=7.15 Hz, 3H) 2.10 (dd, J=7.42, 4.67 Hz, 1H) 2.39 (br s, 1H) 3.45-3.56 (m, 2H) 3.59-3.69 (m, 1H) 3.70-3.80 (m, 3H) 5.86 (d, J=8.25 Hz, 1H) 7.50 (dd, J=7.97, 4.67 Hz, 1H) 8.15 (d, J=7.70 Hz, 1H) 8.76 (d, J=4.40 Hz, 1H), LC-MS 427 (M+H).

Provenance & Evidence