Tetrahydrofuran → HCID 21069288, compound

Participants

Reaction Steps

To a cold (0 C) solution of 2-amino-4-(4-ethoxycarbonylmethoxy-phenyl)-thiophene-3-carboxylic acid ethyl ester hydrochloride salt (1.5 g, 3.90 mmol) in THF (20 mL) was added allylmagnesium chloride (11.7 mL, 23.4 mmol, 2 M solution in THF). The thick slurry was stirred for 0.5 h and was then quenched by the slow addition of saturated NH4Cl (20 mL). The layers were separated, and the aqueous was extracted with EtOAc (3×20 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to a dark oil. The residue was purified by MPLC (SiO2 gel, 3:1 to 2:1 Hz EtOAc) to give the title compound. MS (ESI) m/e 388 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.94 (m, 3H), 2.29 (d, J=7.12 Hz, 4H), 3.70 (m, 2H), 3.96 (q, J=7.12 Hz, 2H), 4.78 (s, 1H), 5.03 (m, 4H), 5.88 (m, 2H), 6.09 (1H), 6.84 (m, 2H), 7.14 (m, 2H), 7.33 (s, 2H).

Provenance & Evidence