4,5-Anhydro-1,3-dideoxy-4-methyl-3-prop-2-en-1-ylpent-2-ulose → 2,4-Dimethyl-3-(prop-2-en-1-yl)furan

HRID 894157Notes

Reaction equation

HRID 894157 reaction equation
[CH2:1]([CH:4]([C:8]1([CH3:11])[O:10][CH2:9]1)[C:5](=O)[CH3:6])[CH:2]=[CH2:3]>C(=O)([O-])[O-].[Na+].[Na+]>[CH3:11][C:8]1[O:10][CH:9]=[C:5]([CH3:6])[C:4]=1[CH2:1][CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 132086284,5-Anhydro-1,3-dideoxy-4-methyl-3-prop-2-en-1-ylpent-2-ulose

Product 1

HCID 132086342,4-Dimethyl-3-(prop-2-en-1-yl)furanYield 45.3%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

3-Allyl-4-methyl-4,5-epoxy-pentan-2-one (4.50 g) was added to a 1% aqueous sodium carbonate solution (150 ml), followed by stirring for 2 hours at a bath temperature of 60° to 65° C. The reaction solution was extracted three times with methylene chloride, and the methylene chloride layer was washed with an aqueous sodium chloride solution. After removing the solvent by evaporation, the residue was column chromatographed on silica gel (50 g) and developed with methylene chloride. From the first eluate (400 ml) was obtained 1.80 g of a pure objective 2,4-dimethyl-3-allylfuran.

Workup

  1. extractionThe reaction solution was extracted three times with methylene chloride
  2. washthe methylene chloride layer was washed with an aqueous sodium chloride solution
  3. customAfter removing the solvent
  4. customby evaporation
  5. customchromatographed on silica gel (50 g)

Sources & evidence

ORD record
ord-6e38610a068c406181689ecfda0b98dd
Source dataset
uspto-grants-1981_08
Patent number
US04282372

Reaction notes

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