1,4-Dioxane → Ethyl acetate hexane

Participants

Reaction Steps

3-(3′-(tert-Butyl)-[1,1′-biphenyl]-3-yl)-6,7-dimethoxy-1-methylisoquinoline (92 mg) and SeO2 (25 mg, 1.2 eq.) in 5 mL anhydrous dioxane were refluxed at 102° C. for 3 hours. Solution was then cooled to room temperature and filtered to remove precipitate. Resulting filtrate was concentrated. Chromatography achieved using ISCO max gradient 30% EtOAc/hexane yielding product as a yellow solid (55 mg, 58% yield). 1H NMR (400 MHz) (CDCl3) δ 10.39 (s, 1H), 8.66 (s, 1H), 8.31 (s, 1H), 8.12 (s, 1H), 8.07 (d, J=4 Hz, 1H), 7.63 (s, 1H), 7.59 (d, J=8 Hz, 1H), 7.53 (t, J=12 Hz, 1H), 7.46-7.44 (m, 1H), 7.36-7.35 (m, 2H), 7.11 (s, 1H), 4.03 (s, 3H), 3.99 (s, 3H), 1.34 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 196.86, 153.26, 152.79, 151.71, 149.69, 147.04, 142.67, 141.02, 139.21, 135.42, 129.29, 128.54, 127.80, 125.81, 125.52, 124.61, 124.54, 124.47, 122.19, 120.07, 104.99, 103.52, 56.31, 56.07, 34.89, 31.47.

Provenance & Evidence