Ammonium Chloride → HCID 118098778, compound

Participants

Reaction Steps

To a solution of 36C (1.803 g, 5.31 mmol) in MeOH (30 mL) and THF (10 mL) was added zinc (dust) (3.47 g, 53.1 mmol) and ammonium chloride (5.68 g, 106 mmol). The resulting solution was stirred at rt for 2 h. MeOH was removed under reduced pressure. Na2CO3 (aq, 100 mL) and EtOAc (150 mL) was added, and the suspension was stirred vigorously for 10 min. The mixture was filtered through a glass frit, solid residue was washed with EtOAc (3×150 mL). Combined EtOAc fractions were washed with std. Na2CO3 (aq, 2×50 mL), water (2×50 mL), brine (1×50 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc/hexanes) to give 36D (1.459 g, 4.72 mmol, 89% yield) as a yellowish oil. MS (ESI) m/z: 310.2 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.29-7.46 (5H, m), 7.15 (1H, br. s.), 6.60 (1H, d, J=7.28 Hz), 6.35-6.55 (1H, m), 5.18 (2H, s), 4.44 (2H, s), 3.71 (2H, br. s.), 3.41-3.66 (2H, m), 2.85 (3H, br. s.).

Provenance & Evidence