Sodium Carbonate → HCID 86588597, compound

Participants

Reaction Steps

A suspension of 134 (0.5 g, 1.0 mmol), benzeneboronic acid (0.15 g, 1.22 mmol), Pd(PPh3)4 and anhydrous Na2CO3 (0.16 g, 1.48 mmol) in distilled benzene (20 mL), water (2 ml) and ethanol (2 mL) was heated at reflux overnight. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (2×20 mL). The organic phase was dried over MgSO4 and evaporated to yield a crude yellow oil. Purification by flash chromatography (ethyl acetate/petroleum ether 30/70 to 70/30) furnished the title compound (0.43 g, 95%): 1H NMR (270 MHz, CDCl3) δ1.98-2.09 (m, 2H); 2.12-2.15 (m, 2H); 3.51-3.62 (m, 2H); 3.7-3.79 (m, 1H); 4.28 (d, J=12.1 Hz, 1H); 4.73 (d, J=4.4 Hz, 1H); 5.18 (d, J=12.1 Hz, 1H); 5.66-5.73 (dd, J=4.8, J=9.8 Hz, 1H); 7.33-7.48 (m, 4H); 7.61-7.70 (m, 3H); 8.02 (d, J=2.2 Hz, 1H). 13C NMR (CDCl3) δ22.9, 28.7, 46.4; 59.8; 75.0; 77.3; 86.0; 94.9; 127.0; 127.3; 128.0; 128.9; 129.6; 130.8; 132.9; 133.5; 139.2; 141.1; 154.4; 166.9. MS: m/e (relative intensity) 468 (M+., 10), 292 (25), 222 (100), 195 (10), 166 (35), 140 (10), 70 (70). HRMS Calculated for C21H19C13N2O4: 468.0411. Found: 468.0410. [α]25D=+103.80 (c=0.42, CHCl3).

Provenance & Evidence