Dimethyl Sulfate → (1-Hydroxy-6-methoxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

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Reaction Steps

To a mixture of (1,6-dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.18 g, 0.64 mmol) and K2CO3 (0.44 g, 3.2 mmol) in acetone was added Me2SO4 (0.16 g, 1.28 mmol). The mixture was stirred at room temperature for 16 hours then diluted with EtOAc. The organic extracts were washed with HCl (aq), dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give (1-hydroxy-6-methoxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.060 g, 32%). 1H NMR (400 MHz, MeOD-d4) δ 7.08 (s, 1H), 6.99 (s, 1H), 5.62 (m, 1H), 5.50 (m, 2H), 4.08 (m, 2H), 3.80 (s, 3H), 3.37 (s, 3H), 3.12 (m, 1H), 2.17 (m, 1H), 1.20 (m, 3H).

Provenance & Evidence