Ammonia → 3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole

Participants

Reaction Conditions

Reaction Steps

To a sealed vessel were charged 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trimethylsilyl)isoxazole (169 g, 0.569 mol), 25% aqueous ammonia (1500 mL), and ethanol (1500 mL). The reaction mixture was heated to 60° C. After 6 hours, the reaction mixture was concentrated under reduced pressure. The residue was purified via chromatography on silica gel (0-5% methanol/dichloromethane, linear gradient) to give 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole. MS ESI calc'd. for C10H16BNO3 [M]+ 209. found 209. 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 2.40 (s, 3H), 1.31 (s, 12H).

Provenance & Evidence