Tetrahydrofuran → 6-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418948Notes

Reaction equation

HRID 418948 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]OS(C1C=CC(C)=CC=1)(=O)=O)[CH:12]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH3:17])[CH:12]([C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 72309434Toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester

Product 1

HCID 666519736-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthreneYield 85.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester (0.471 g, 0.93 mmol), lithium aluminum hydride (0.069 g, 1.86 mmol), and tetrahydrofuran (8.0 mL), and reflux under nitrogen atmosphere. After 5 hours, quench reaction by adding reaction to a stirred solution of Rochelle's salt (Na K Tartrate) and ethyl acetate. After several hours, separate the organic phase and wash with brine. Dry the organic phase with anhydrous sodium sulfate and flash chromatograph using 0% to 20% ethyl acetate/hexanes to yield the titled compound (0.267 g, 85%) as a white solid. TLC Rf=0.43 in 3:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.35 (d, 1H, J=8.4 Hz), 7.23 (d, 2H, J=8.4 Hz), 6.94 (m, 3H), 6.82 (dd, 1H, J=8.8, 2.6 Hz), 3.86 (s, 6H), 3.31 (m, 2H), 2.82 (dd, 1H, J=11.9, 2.6 Hz), 2.50 (d, 1H, J=13.7 Hz), 1.89 (m, 1H), 1.64 (m, 2H), 1.44 (m, 2H), 1.16 (m, 6H).

Workup

  1. customquench
  2. customreaction
  3. additionby adding
  4. waitAfter several hours
  5. customseparate the organic phase
  6. washwash with brine
  7. dry with materialDry the organic phase with anhydrous sodium sulfate and flash chromatograph

Sources & evidence

ORD record
ord-b4e5c1b6e28947bf914efff539673bc8
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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