Acetic Acid → HCID 86727438, compound

Participants

Reaction Steps

To a solution of 4-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.500 g, 0.923 mmol) in dioxane (25 mL) was added AcOH (2.5 mL) and hydrogen peroxide (30%, 5 mL) and the reaction mixture was stirred at ambient temperature overnight. The solution was quenched by the addition of saturated Na2SO3 solution and the volatiles were evaporated in vacuo. The aqueous residue was extracted with EtOAc (3×20 mL) and the combined organic phases were dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 5-20% EtOAc in petroleum ether) to give 6-hydroxy-4-methyl-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.200 g, 50%) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.15 (s, 1H), 6.59 (s, 1H), 6.00 (s, 1H), 5.14 (m, 2H), 4.69 (m, 2H), 4.56 (m, 1H), 3.69 (t, J=8.4 Hz, 2H), 1.53 (d, J=6.4 Hz, 3H), 1.02 (m, 2H), 0.04 (s, 9H).

Provenance & Evidence