Reaction #94742

ord-993773ea68ff4fe1ad96bbc9c751b379

Reaction equation

[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
COc1ccc(CC(CCC2(CCc3ccc(C)cc3)OCCO2)[N+](=O)[O-])cc1OC
1-(3,4-dimethoxyphenyl)-2-nitro-7-(4-methylphenyl)-5-heptanone ethylene ketal
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
O=S(=O)([O-])[O-].[Na+].[Na+]
Na2SO4
→
COc1ccc(CC(N)CCC2(CCc3ccc(C)cc3)OCCO2)cc1OC
brown oil
Yield 96.1%
COc1ccc(CC(N)CCC2(CCc3ccc(C)cc3)OCCO2)cc1OC
1-(3',4'-Dimethoxyphenyl)-2-amino-7-(4'-methylphenyl)-5-heptanone ethylene ketal
Yield 96.1%

Reactants

[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
—
3
COc1ccc(CC(CCC2(CCc3ccc(C)cc3)OCCO2)[N+](=O)[O-])cc1OC
1-(3,4-dimethoxyphenyl)-2-nitro-7-(4-methylphenyl)-5-heptanone ethylene ketal
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
O=S(=O)([O-])[O-].[Na+].[Na+]
Na2SO4

Reagents

None

Solvents

C1CCOC1
THF
C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONcondensor and addition funnel
  2. 2
    TemperatureThe reaction was refluxed for 2 hours
  3. 3
    Filtrationthe salts filtered
  4. 4
    Dryingthe organic layer dried over MgSO4
  5. 5
    Filtrationfiltered
  6. 6
    Concentrationconcentrated

Procedure

In a 500 mL 3 necked rb flask equipped with a mechanical stirrer, condensor and addition funnel, a THF solution of 1-(3,4-dimethoxyphenyl)-2-nitro-7-(4-methylphenyl)-5-heptanone ethylene ketal (15.7 g; 0.037 mole) was added slowly to a suspension of LiAlH4 (14.2 g; 0.111 mole) in dry THF. The reaction was refluxed for 2 hours. Excess LiAlH4 was then decomposed with sat. Na2SO4, the salts filtered and the organic layer dried over MgSO4, filtered and concentrated to yield 14.2 g of a brown oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04342692uspto-grants-1982_08