Water → HCID 15384498, compound

HRID 1004159Notes

Reaction equation

HRID 1004159 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[CH:7][O:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C1C=CC=CC=1>[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([Br:11])[O:6][C:5]=1[CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5796763-Acetyl-2,4-dimethylfuran

Product 1

HCID 15384498HCID 15384498, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-acetyl-2,4-dimethylfuran (commercially available from Aldrich Chemical Co., Inc., 1 g, 7.24 mmol), N-bromosuccinimide (NBS; 1.3 g, 7.3 mmol), and 2,2'-azobisisobutyronitrile (AIBN; 3 mg) in benzene (10 mL) was heated at reflux temperature for one hour. After cooling, water (50 mL) was added to the mixture. The whole was extracted with benzene (50 mL), the organic layer washed with water, brine, dried over MgSO4, and concentrated in vacuo. Chromatographic purification of the residue eluting with ethyl acetate-hexane (1:10) provided the subtitle compound (1.38 g, 88% yield) as a pale yellow oil.

Workup

  1. temperatureat reflux temperature for one hour
  2. temperatureAfter cooling
  3. extractionThe whole was extracted with benzene (50 mL)
  4. washthe organic layer washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the residue
  8. washeluting with ethyl acetate-hexane (1:10)

Sources & evidence

ORD record
ord-16b69e0e5d2e4620825207db1a48e07b
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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