Methyl Gallate → Methyl 3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzoate

Participants

Reaction Steps

To a solution in which the 2-(2-(2-azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (4.80 g, 14.57 mmol) compound of Chemical Formula 9 was dissolved in acetone (15 mL), K2CO3 (2.05 g, 14.85 mmol), the methyl gallate (650.9 mg, 3.53 mmol) compound of Chemical Formula 10 and tetrabutylammonium bromide (25 mg) were added consecutively at room temperature. The reaction mixture was heated under reflux for 17 hours, cooled to room temperature, and partitioned to distilled water (40 mL) and ethyl acetate (150 mL). The organic layer was separated, washed with saturated salted water (15 mL), dried with anhydrous sodium sulfate, filtered and vacuum distilled, and the residue obtained was column chromatographed on silica gel (hexane/ethyl acetate (1:1.5)) to give methyl 3,4,5-tris(2-(2-(2-azidoethoxy)ethoxy)ethoxy)benzoate (2.18 g, 94%). 1H NMR (500 MHz, CDCl3) δ 7.29 (s, 2H), 4.18-4.23 (m, 6H), 3.86-3.88 (m, 7H), 3.81 (t, 2H, J=5.0 Hz), 3.70-3.74 (m, 6H), 3.63-3.67 (m, 12H), 3.36-3.39 (m, 6H).

Provenance & Evidence