Benzyl Bromide → 3-Benzyloxy-2-methyl-4-pyrone

Participants

Reaction Conditions

Reaction Steps

To a 500 mL flask with 10.0 g (0.08 mol) of maltol (3-hydroxy-2-methyl-4H-pyran-4-one) in 120 mL of anhydrous DMF was added 14.1 mL (0.12 mol) of benzyl bromide and potassium carbonate (16.4 g, 0.12 mol) and heated at 80° C. overnight. After cooling to room temperature, the reaction was filtered and the solvents evaporated. The residual oil was brought up in 100 mL CH2Cl2 and washed twice with a saturated NaHCO3 solution, water, and brine. The organic layer was dried over MgSO4, filtered and concentrated. Product was purified on a silica gel column eluting with 0.5% MeOH in CH2Cl2 to yield a pale yellow solid in 75% yield (12.8 g, 59 mmol). 1H NMR (400 MHz, CDCl3) δ=7.59 (d, J=5.6 Hz, 1H), 7.36 (m, 5H), 6.36 (d, J=5.6 Hz, 1H), 5.15 (s, 2H, OCH2), 2.08 (s, 3H, CH3). ESI-MS(+): m/z 217.03 [M+H]+, 239.07 [M+Na]+.

Provenance & Evidence