Acetic Anhydride → 6-Methoxy-5-nitro-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one

Participants

Reaction Steps

Combine 6-methoxy-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one (0.936 g, 4.06 mmol), Ac2O (5.0 mL), and a solution of 90% HNO3/acetic acid (0.8 mL), and stir under Nitrogen atmosphere at 0° C. After 3 hours, add ethyl acetate. Wash the ethyl acetate with sodium bicarbonate solution and then brine, dry over sodium sulfate, and concentrate in vacuum. Flash chromatograph using dichloromethane (isocratic) to yield the titled compound (0.378 g, 34%) as a solid. TLC Rf=0.25 in dichlormethane. 1H NMR (CDCl3): 8.22 (d, 1H, J=8.8 Hz), 7.04 (d, 1H, J=8.8 Hz), 3.99 (s, 3H), 2.96 (m, 2H), 2.49 (m, 2H), 1.63 (m, 8H).

Provenance & Evidence