Methyl vinyl ketone → HCID 21072001, compound

HRID 1372495Notes

Reaction equation

HRID 1372495 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])[CH:9]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8]2)(=[O:3])[CH3:2].C[O-:20].[Na+].[CH:22]([C:24]([CH3:26])=O)=[CH2:23]>CO>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[C:9]([CH2:23][CH2:22][CH2:24][CH3:26])([CH2:15][CH2:16][C:17](=[O:20])[CH3:18])[CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 10942334Sodium MethoxideHCID 17972753HCID 17972753, compound

Product 1

HCID 21072001HCID 21072001, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 5-(acetylamino)-2-butyl-1-indanone (8.8 g, 35.9 mmol) in MeOH (95 mL) was treated with 0.5M NaOMe in MeOH (14.4 mL, 7.2 mmol). The resulting solution was placed under a N2 atmosphere, treated with methyl vinyl ketone (4.5 mL, 54 mmol), and then stirred at room temperature for three days. The mixture was partitioned between EtOAc and saturated aqueous NH4Cl, and the aqueous phase was back-extracted with EtOAc. The combined organics were washed with 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated under vacuum to an oil (11.8 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 provide 5-(acetylamino)-2-butyl-2-(3-oxobutyl)-1-indanone (9.8 g, 87%) as a clear oil.

Workup

  1. customThe mixture was partitioned between EtOAc and saturated aqueous NH4Cl
  2. extractionthe aqueous phase was back-extracted with EtOAc
  3. washThe combined organics were washed with 5% NaHCO3, water, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum to an oil (11.8 g)
  7. customThe crude product was purified by Biotage flash chromatography on a 75 L silica gel column (7.5×35 cm)
  8. washeluting with 2:1 hexane-EtOAc

Sources & evidence

ORD record
ord-4b7b48d956f64df8a4b9da548682649d
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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