Ethyl Acetate → HCID 9903701, compound

Participants

Reaction Steps

Cd/Pb (0.47 g) couple was added portion wise to a vigorously stirred solution of 135 (0.33 g, 0.7 mmol) in THF (5 mL) and of aq. ammonium acetate (1M, 5 mL). The suspension was allowed to stir at room temperature for 2 hours, then poured into ethyl acetate (200 mL), dried with MgSO4 and filtered. The filtrate was evaporated and the residue purified by flash column chromatography (ethyl acetate) to afford the title compound as colourless oil (0.19 g, 98%): 1H NMR (270 MHz, CDCl3) δ2.0-2.12 (m, 2H); 2.29-2.37 (m, 2H); 3.53-3.63 (m, 1H); 3.76-3.92 (m, 2H); 7.36-7.79 (m, 8H); 8.28 (d, J=2.2 Hz, 1H). 13C NMR (67.8 MHz, CDCl3) δ24.4; 29.8; 46.9; 53.8; 126.9; 127.3; 127.7; 128.0; 128.2; 128.8; 128.9; 129.1; 130.1; 130.5; 139.5; 145.0; 164.5; 165.1. IR (Nujol): cm−1 3000-2800, 1620, 1455, 1377, 1239, 1239, 1014, 990, 761,728, 697. HRMS Calculated for C18H16N2O: 276.1261. Found: 276.1262. [α]25D=+131.4° (c=0.19, CHCl3).

Provenance & Evidence