Sodium borohydride → HCID 67491614, compound

Participants

Reaction Steps

Referring to FIG. 20, NaBH4 (0.0028 g, 0.074 mmol) was added to a solution of 9c (0.0397 g, 0.158 mmol) in ethanol (4 mL). The mixture was stirred for 20 min. The solvent was evaporated, and the resulting solid residue was dissolved in chloroform, then washed with water (×2) followed by brine, dried over MgSO4, and concentrated to afford 10c (0.0396 g, 0.156 mmol, 99%) as a white, crystalline solid (mp 84-87° C.): 1H NMR (CDCl3) δ 8.09 (1H, d, J=8.4 Hz), 7.71 (1H, d, J=8.8 Hz), 7.52 (1H, d, J=9.2 Hz), 7.24 (1H, d, J=8.4 Hz), 5.41 (2H, s), 4.94 (2H, s) 3.58 (3H, s); 13C NMR (CDCl3) δ 160.3, 154.2, 144.1, 137.2, 127.0, 124.4, 120.0, 117.4, 117.2, 95.7, 64.4, 56.8; FTIR (neat) 3342, 2925, 1615, 1155, 1005, 835, 781 cm−1; MS (ESI) m/z calculated for (C12H12ClNO3+H)+ 254 (35Cl) and 256 (37Cl), found 254 (35Cl) and 256 (37Cl); HRMS (ESI) m/z calculated for (C12H12ClNO3+H)+ 254.0584 (35Cl) and 256.0554 (37Cl), found 254.0577 (35Cl) and 256.0546 (37Cl).

Provenance & Evidence