1,4-Dioxane → 2a-(3-Formylpropyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

HRID 2301133Notes

Reaction equation

HRID 2301133 reaction equation
[CH2:1]([C:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18])[CH2:2][CH2:3][CH:4]=C.C[N+]1([O-])CC[O:23]CC1.O1CCOCC1.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O>[CH:4]([CH2:3][CH2:2][CH2:1][C:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18])=[O:23]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 82029Methyl morpholine oxideHCID 3732662a-(4-Pentenyl)-2a,3,4,5-tetrahydrobenzo[cd]indol-2(1H)-oneHCID 23667635Sodium periodate

Product 1

HCID 155426362a-(3-Formylpropyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

In a shaded container, 2a-(4-pentenyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (1.3 g, 5.3 mmol) and N-methylmorpholine oxide (1.9 g, 16 mmol) were dissolved in a mixed solvent of 1,4-dioxane (20 ml) with water (10 ml), and the solution was mixed with osmium tetroxide (4% aqueous solution 3.4 ml, 0.53 mmol) and stirred at room temperature for 2 hours. The reaction solution was mixed with rater (80 ml), the reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate, and then the solvent was removed by evaporation under a reduced pressure. The residue was dissolved in a mixed solvent of 1,4-dioxane (20 ml) with water (10 ml), and the solution was mixed with sodium periodate (2.6 g, 12 mmol) and stirred as such for 2.5 hours. The reaction solution was mixed with water (100 ml), and the reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate. By evaporating the solvent from the extract under a reduced pressure, 1.3 g (5.3 mmol 100% in yield) of the title compound was obtained.

Workup

  1. additionThe reaction solution was mixed with rater (80 ml)
  2. extractionthe reaction product was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under a reduced pressure
  6. dissolutionThe residue was dissolved in a mixed solvent of 1,4-dioxane (20 ml) with water (10 ml)
  7. stirringstirred as such for 2.5 hours
  8. extractionthe reaction product was extracted with ethyl acetate
  9. washwashed with saturated brine
  10. dry with materialdried with anhydrous sodium sulfate
  11. customBy evaporating the solvent from the
  12. extractionextract under a reduced pressure, 1.3 g (5.3 mmol 100% in yield) of the title compound
  13. customwas obtained

Sources & evidence

ORD record
ord-507c26db555f4702910a2c6c7488aa33
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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