Tetrahydrofuran → [6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-methanol

HRID 418946Notes

Reaction equation

HRID 418946 reaction equation
C[O:2][C:3]([CH:5]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([O:27][CH3:28])[CH:10]=2)=O.[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>[CH3:28][O:27][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]([CH2:3][OH:2])[CH:18]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH:17]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 666520266-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester

Product 1

HCID 66651951[6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester (4.25 g, 11.17 mmol), lithium aluminum hydride (1.20 g, 32.39 mmol), and tetrahydrofuran (150 mL), and reflux under nitrogen atmosphere. After 3 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 5% to 30% ethyl acetate/hexanes to yield the titled compound (3.54 g, 90%) as a white solid. TLC Rf=0.13 in 4:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.43 (d, 1H, J=8.8 Hz), 7.26 (d, 2H, J=8.4 Hz), 7.00 (m, 1H), 6.93 (d, 2H, J=8.8 Hz), 6.84 (dd, 1H, J=8.4, 2.6 Hz), 4.05 (dd, 1H, J=11.2, 3.3 Hz), 3.86 (m, 6H), 3.62 (dd, 1H, J=11.0, 2.6 Hz), 3.34 (m, 3H), 2.49 (d, 1H, J=13.7 Hz), 1.95 (m, 1H), 1.65 (m, 2H), 1.45 (m, 2H), 1.30 (m, 1H), 1.16 (m, 2H).

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-caaca8f3f1d445cba0c95840d56ef843
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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