Sodium Hydroxide → 4-(2-Hydroxyethoxy)-2-methoxyphenyl acetate

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A solution of 1-acetyl-1H-1,2,3-triazolo[4,5-b]pyridine (0.248 g, 1.532 mmol) in dry THF (6.13 mL) was added to a solution of 4-(2-hydroxyethoxy)-2-methoxyphenol (0,2821 g, 1.532 mmol) in 1N aq. NaOH (1.532 mL, 1.532 mmol) at 25° C. The reaction was stirred at 25° C. for 3 h. The reaction was diluted with 1IN HCl (20 mL) and extracted with Et2O (3×20 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 50% EtOAc in hexanes over 360 mL, gradient to 100% EtOAc over 2034 mL) to afford 4-(2-hydroxyethoxy)-2-methoxyphenyl acetate. Rf=0.28 (50% EtOAc/hexanes). LCMS calc.=249.1; found=249.0 (M+Na)+. 1H NMR (500 MHz, CHCl3): δ 6.87 (d, J=8.7 Hz, 1 H); 6.52 (d, J=2.7 Hz, 1 H); 6.38 (dd, J=8.7, 2.7 Hz, 1 H); 3.96 (t, J=4.7 Hz, 2 H); 3.84 (t, J=4.7 Hz, 2 H); 3.71 (s, 3 H); 2.97 (s, 1 H); 2.24 (s, 3 H).

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