Aluminum isopropoxide → HCID 22464448, compound

HRID 1655332Notes

Reaction equation

HRID 1655332 reaction equation
CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[O:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[N:16]1[CH:25]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27]>C(O)(C)C>[O:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[N:16]1[CH:25]([CH2:34][CH:35]([CH3:37])[CH3:36])[CH:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[OH:27]

Participants

4

Reactant 2

HCID 11143Aluminum isopropoxideHCID 197916912-(1,3-Dioxo-2-azaindan-2-yl)-4-methyl-1-phenylpentan-1-one

Product 1

HCID 22464448HCID 22464448, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Aluminum isopropoxide (125.6 g, 615 mmol) was added to a suspension of 2-(1,3-dioxo-2-azaindan-2-yl)-4-methyl-1-phenylpentan-1-one (72.3 g, 225 mmol) in isopropanol (1,000 ml). The mixture was heated under reflux for 6.5 hours. The isopropanol was removed by distillation under reduced pressure and to the residue were added ethyl acetate (800 ml) and an aqueous solution of sodium sulfate. The resulting organic layer was decanted and the residue was washed twice with ethyl acetate (200 ml). The combined organic layer was washed with brine. The organic solution was dried and the solvent was removed by distillation under reduced pressure. The residue was recrystallized twice from benzene to obtain 29.3 g of the title compound as white crystals (yield: 40%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6.5 hours
  3. customThe isopropanol was removed by distillation under reduced pressure and to the residue
  4. additionwere added ethyl acetate (800 ml)
  5. customThe resulting organic layer was decanted
  6. washthe residue was washed twice with ethyl acetate (200 ml)
  7. washThe combined organic layer was washed with brine
  8. customThe organic solution was dried
  9. customthe solvent was removed by distillation under reduced pressure
  10. customThe residue was recrystallized twice from benzene

Sources & evidence

ORD record
ord-c3c7ad16683b4334b60cfa1efa66e11f
Source dataset
uspto-grants-1993_10
Patent number
US05250546

Reaction notes

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