Dimethylformamide → HCID 58858118, compound

Participants

Reaction Steps

A solution of 4-nitroguaiacol potassium salt (613 mg; 2.96 mmol) and t-butyl bromoacetate (0.65 mL; 4.43 mmol) in DMF (7 mL) was stirred at rt for 0.5 h prior to dilution with H2O and extraction with EtOAc. The organic layer was washed with H2O, dried over MgSO4, filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, Hexanes/EtOAc, 100:0 to 1:1 gradient) to afford the title compound (738 mg; 88%) as a beige solid. 1H NMR (CDCl3) δ 1.46 (s, 9H), 3.96 (s, 3H), 4.67 (s, 2H), 6.77 (d, J=8.79 Hz, 1H), 7.76 (d, J=2.74 Hz, 1H), 7.85 (dd, J=8.80 Hz, 2.75 Hz, 1H); 13C NMR (CDCl3) δ 27.98, 56.37, 66.18, 83.09, 107.07, 111.52, 117.28, 142.17, 149.19, 152.69, 166.66; HPLC (Method #1): 3.13 min retention time, (97%); MS (ES): m/z 306 [M+Na]+.

Provenance & Evidence