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

反応式

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

参加物

反応物 4

HCID 313Hydrochloric Acid

HCID 8857Ethyl Acetate

HCID 10942334Sodium Methoxide

HCID 666520557-Bromo-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

生成物 1

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

実験手順

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).