Toluene → HCID 66651903, compound

HRID 418958Notes

Reaction equation

HRID 418958 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:26]([O-:28])=[O:27])=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13](O)[CH:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]([N+:26]([O-:28])=[O:27])=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 66652375HCID 66652375, compound

Product 1

HCID 66651903HCID 66651903, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  1. temperaturereflux under nitrogen atmosphere
  2. temperaturecool
  3. customreaction to ambient temperature
  4. washwash
  5. dry with materialwith brine, dry over sodium sulfate
  6. concentrationconcentrate in vacuum

Sources & evidence

ORD record
ord-cf87ad9a481741dc86edcd7062b4bac4
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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