Maltol → HCID 54767214, compound

Participants

Reaction Steps

Maltol (0.50 g, 3.96 mmol) was dissolved in 25 mL of acetonitrile followed by the addition of 1.6 g (11.88 mmol) of K2CO3. The reaction was heated to reflux for 10 min before adding 4-bromomethylphenyl boronic acid pinacol ester (1.3 g, 4.4 mmol). The reaction was left stirring under refluxing conditions for 12 h then cooled to room temperature and filtered rinsing with DCM. The resulting filtrate was concentrated and purified via silica gel chromatography eluting with 0-2% MeOH in DCM. B20 (1.03 g, 3.0 mmol) was collected and dried yielding a pale yellow solid in 76% yield. 1H NMR (400 MHz, CDCl3) δ=7.77 (d, J=7.6 Hz, 2H), 7.58 (d, J=5.2 Hz, 1H), 7.37 (d, J=7.6 Hz, 2H), 6.35 (d, J=5.6 Hz, 1H), 5.19 (s, 2H), 2.06 (s, 3H), 1.34 (s, 12H). 13C NMR (100 MHz, CDCl3) δ=175.3, 160.0, 153.6, 143.9, 140.0, 135.1, 128.5, 117.4, 84.1, 73.6, 25.1, 15.2. ESI-MS(+): m/z 343.18 [M+H]+. Anal. calcd. for C19H23BO5: C, 66.69; H, 6.77. Found: C, 66.34; H, 6.67.

Provenance & Evidence