Toluene → HCID 66651903, compound

Participants

Reaction Steps

Combine 6-methoxy-10-(4-methoxy-phenyl)-5-nitro-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ol (378.6 mg, 0.987 mmol), p-toluene sulfonic acid (38.0 mg, 0.197 mmol), toluene (8 mL), stir, and reflux under nitrogen atmosphere. After 1 hour, cool reaction to ambient temperature, add ethyl acetate, wash sat sodium bicarbonate solution (aq), and then with brine, dry over sodium sulfate, and concentrate in vacuum. Flash chromatograph using 0% to 30% ethyl acetate/hexanes to yield the titled compound (234.5 mg, 68%) as a clear oil. TLC Rf=0.40 in 2:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.25 (d, 2H, J=8.4 Hz), 6.91 (d, 2H, J=8.4 Hz), 6.67 (d, 1H, J=8.4 Hz), 6.58 (d, 1H, J=8.4 Hz), 6.37 (d, 1H, J=2.6 Hz), 3.88 (m, 614), 3.18 (s, 1H), 2.90 (m, 1H), 2.19 (d, 1H, J=14.1 Hz), 1.60 (m, 4H), 1.33 (m, 2H), 0.99 (m, 1H).

Provenance & Evidence