Methyl iodide → 6-Methoxy-9-methoxymethyl-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418953Notes

Reaction equation

HRID 418953 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][OH:18])[CH:12]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[H-].[Na+].[CH3:29]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][O:18][CH3:29])[CH:12]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66651951[6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-methanol

Product 1

HCID 666519026-Methoxy-9-methoxymethyl-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthreneYield 216%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine [6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-methanol (0.084 g, 0.24 mmol), NaH (0.014 mg, 0.29 mmol), and DMF (3.0 mL) and stir under nitrogen atmosphere at −10° C. After 1 hour, add MeI (50 uL, 0.072 mmol) and stir at room temperature for 18 hours. Concentrate reaction under vacuum then add ethyl acetate and water, separated the organic phase and wash 2× with brine. Dry the organic phase over anhydrous sodium sulfate. Concentrate the organic phase under vacuum and flash chromatograph using 0% to 25% ethyl acetate/hexanes to yield the titled compound (0.057 g, 65%) as a white solid. TLC Rf=0.40 in 3:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.58 (d, 1H, J=8.8 Hz), 7.25 (d, 2H, J=8.8 Hz), 6.93 (m, 3H), 6.81 (dd, 1H, J=8.4, 2.6 Hz), 3.85 (m, 6H), 3.66 (m, 1H), 3.38 (m, 2H), 3.23 (m, 4H), 3.11 (dd, 1H, J=11.9, 3.1 Hz), 2.48 (d, 1H, J=13.7 Hz), 1.92 (m, 1H), 1.42 (m, 2H), 1.18 (m, 3H), 1.77 (m, 2H).

Workup

  1. concentrationConcentrate
  2. customreaction under vacuum
  3. customadd ethyl acetate and water, separated the organic phase
  4. washwash 2× with brine
  5. dry with materialDry the organic phase over anhydrous sodium sulfate
  6. concentrationConcentrate the organic phase under vacuum and flash chromatograph

Sources & evidence

ORD record
ord-99055db7092e471092b8e6b6c7cb7d5a
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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