Water → HCID 15384498, compound

HRID 2121703Notes

Reaction equation

HRID 2121703 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-18ecf44f80684a4abb41f298ab806220
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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