Ethyl cyanoacetate → HCID 118101219, compound

Participants

Reaction Conditions

Reaction Steps

36A (3.000 g, 7.91 mmol), copper(I) iodide (0.301 g, 1.582 mmol), L-proline (0.364 g, 3.16 mmol) and cesium carbonate (5.16 g, 15.82 mmol) were mixed in a pressure vial and degassed (3× vacuum/Ar). Then, a solution of ethyl 2-cyanoacetate (1.059 mL, 9.89 mmol) in DMSO (10 mL) was added, the reaction mixture was degassed again and stirred at 50° C. for 3 days. The cooled reaction mixture was partitioned between EtOAc (100 mL) and sat. NH4Cl (100 mL). The organic layer was washed with brine (2×50 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography to give 36B (2.609 g, 6.34 mmol, 80% yield) as a yellowish syrup. MS (ESI) m/z: 412.2 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 8.24 (1H, d, J=8.03 Hz), 8.14 (1H, br. s.), 7.79 (1H, d, J=8.53 Hz), 7.29-7.43 (5H, m), 5.67 (1H, br. s.), 5.18 (2H, s), 4.50-4.86 (2H, m), 4.14-4.29 (2H, m), 2.90 (3H, s), 1.27 (3H, t, J=7.15 Hz).

Provenance & Evidence