Hydrochloric Acid → 6,7-Dimethoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418937Notes

Reaction equation

HRID 418937 reaction equation
Br[C:2]1[CH:15]=[C:14]2[C:5]([CH:6]3[CH:11]([CH:12]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[CH2:13]2)[CH2:10][CH2:9][CH2:8][CH2:7]3)=[CH:4][C:3]=1[O:24][CH3:25].C[O-].[Na+].[C:29](OCC)(=[O:31])C.Cl>>[CH3:25][O:24][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:2]=1[O:31][CH3:29])[CH2:13][CH:12]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 666520557-Bromo-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

Product 1

HCID 723094246,7-Dimethoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthreneYield 68.1%

Procedure

Combine 7-Bromo-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (chiral) (0.025 g, 0.06 mmol), NaOMe 5N (1.4 ml, 7 mmol), CuIBr (0.005 g, 0.034 mmol) and ethyl acetate (0.005 ml, 0.05 mmol) and heat at 115° C. for 1.5 hours. Cool, and add 1N HCl and extract with ethyl acetate. Wash organic layer with water, dry over anhydrous sodium sulfate and remove solvent in vacuo. Chromatograph on silica gel with 9% ethyl acetate/hexanes to yield the titled compound (0.012 g, 55%). 1H NMR (CDCl3). MS m/z 352.9 (M+1).

Workup

  1. temperatureCool
  2. extractionextract with ethyl acetate
  3. dry with materialWash organic layer with water, dry over anhydrous sodium sulfate
  4. customremove solvent in vacuo

Sources & evidence

ORD record
ord-fece7a1c8e534f0cb61a7865c3b66cf4
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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