Ethanol → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ol

HRID 418896Notes

Reaction equation

HRID 418896 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[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.[BH4-].[Na+].C(O)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([OH:17])[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

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 666519296-Methoxy-10-(4-methoxy-phenyl)-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one

Product 1

HCID 666520046-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 6-methoxy-10-(4-methoxy-phenyl)-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one (58.0 mg, 0.17 mmol), sodium borohydride (52.0 mg, 1.40 mmol), ethanol (3.0 mL), tetrahydrofuran (3.0 mL), stir, and reflux under a nitrogen atmosphere. After 2 hours, cool to ambient temperature, and concentrate in vacuo. Add ethyl acetate to reaction mixture, wash with sat ammonium chloride solution(aq), Brine, and dry over sodium sulfate. Concentrate to yield the titled compound (57.0 mg, 99%) as a white solid. TLC Rf=0.12 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.50 (d, 1H, J=8.8 Hz), 7.20 (d, 2H, J=8.4 Hz), 6.93 (d, 2H, J=8.4 Hz), 6.80 (dd, 1H, J=8.6, 2.4 Hz), 6.66 (m, 1H), 4.77 (d, 1H, J=9.7 Hz), 3.82 (m, 6H), 3.05 (m, 1H), 2.85 (m, 1H), 2.35 (m, 1H), 1.75 (m, 4H), 1.40 (m, 5H).

Workup

  1. temperaturereflux under a nitrogen atmosphere
  2. concentrationconcentrate in vacuo
  3. customAdd ethyl acetate to reaction mixture
  4. washwash with sat ammonium chloride solution(aq), Brine
  5. dry with materialdry over sodium sulfate
  6. concentrationConcentrate

Sources & evidence

ORD record
ord-79cda89c807a40c9a11600c944dfd5a5
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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