Ammonium Chloride → HCID 118098736, compound

Participants

Reaction Steps

To a solution of 17E (2.789 g, 7.14 mmol) in methanol (40 mL) and THF (10 mL) was added zinc (dust) (4.67 g, 71.4 mmol) and ammonium chloride (7.64 g, 143 mmol). The resulting solution was stirred at rt for 30 min, then at 40° C. overnight. MeOH was removed under reduced pressure, Na2CO3 (aq, 100 mL) and EtOAc (150 mL) were added, and the suspension was stirred vigorously for 10 min. The mixture was filtered though glass frit, solid residue was washed with EtOAc (3×150 mL). Combined EtOAc fractions were washed with sat. 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). Fractions were combined and concentrated under reduced pressure to give 17F (2.566 g, 7.12 mmol, 100% yield) as a yellowish oil, which solidified upon standing. MS (ESI) m/z: 361.1 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.30-7.46 (5H, m), 6.37 (1H, dd, J=12.55, 2.76 Hz), 6.11-6.30 (1H, m), 4.94 (2H, s), 4.20-4.39 (2H, m), 3.58 (2H, s), 2.70 (3H, d, J=7.53 Hz), 1.36-1.54 (9H, m).

Provenance & Evidence