Butanal → HCID 17972753, compound

HRID 1372494Notes

Reaction equation

HRID 1372494 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].[OH-].[K+].[CH:17](=O)[CH2:18][CH2:19][CH3:20]>CCO.[Pd]>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH:9]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 261ButanalHCID 14797Potassium HydroxideHCID 312894N-(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 17972753HCID 17972753, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(Acetylamino)-1-indanone (10.0 g, 52.3 mmol) was added to a solution of KOH (87.7%, 0.66 g, 10.3 mmol) in EtOH (200 mL). The resulting suspension was stirred at room temperature while butyraldehyde (6.1 mL, 67.8 mmol) was added dropwise over two minutes. After stirring at room temperature for an additional 15 minutes, the mixture was treated with 10% Pd/C and stirred under a H2 atmosphere (balloon) for 19 hours. The mixture was filtered through a pad of silica gel and the pad washed with EtOAc. The filtrate was washed with 1N HCl, 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated under vacuum to an orange oil (12 g). The crude product was purified by Biotage flash chromatography on a 75 L silica gel column (7.5×35 cm), eluting with 2:1 hexane-EtOAc, to afford 5-(acetylamino)-2-butyl-1-indanone (8.8 g, 69%) as a clear oil.

Workup

  1. additionwas added dropwise over two minutes
  2. stirringstirred under a H2 atmosphere (balloon) for 19 hours
  3. filtrationThe mixture was filtered through a pad of silica gel
  4. washthe pad washed with EtOAc
  5. washThe filtrate was washed with 1N HCl, 5% NaHCO3, water, and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum to an orange oil (12 g)
  9. customThe crude product was purified by Biotage flash chromatography on a 75 L silica gel column (7.5×35 cm)
  10. washeluting with 2:1 hexane-EtOAc

Sources & evidence

ORD record
ord-ae3ff0003c904ecc866f1313808507f0
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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