m-Chloroperbenzoic acid → 4,5-Anhydro-1,3-dideoxy-4-methyl-3-prop-2-en-1-ylpent-2-ulose

HRID 894159Notes

Reaction equation

HRID 894159 reaction equation
[CH2:1]([CH:4]([C:8]([CH3:10])=[CH2:9])[C:5](=[O:7])[CH3:6])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)Cl>[CH2:1]([CH:4]([C:8]1([CH3:10])[O:19][CH2:9]1)[C:5](=[O:7])[CH3:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 132086223-(Prop-1-en-2-yl)hex-5-en-2-one

Product 1

HCID 132086284,5-Anhydro-1,3-dideoxy-4-methyl-3-prop-2-en-1-ylpent-2-uloseYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-allyl-4-methyl-pent-4-en-2-one (20.0 g) in methylene chloride (100 ml) was added dropwise a solution of m-chloroperbenzoic acid (29 g) in methylene chloride (300 ml) at 0° to 5° C. The reaction mixture was stirred at 0° to 5° C. for 3 hours and then at 20° C. overnight. The reaction solution was progressively washed with an aqueous sodium hydrogen carbonate solution, aqueous sodium sulfite solution, aqueous sodium hydrogen carbonate solution and then with an aqueous sodium chloride solution. After removing the solvent by evaporation, the residue was distilled to obtain 7.2 g of the unreacted material and 5.2 g of the objective 3-allyl-4-methyl-4,5-epoxy-pentan-2-one.

Workup

  1. customat 20° C.
  2. customovernight
  3. washThe reaction solution was progressively washed with an aqueous sodium hydrogen carbonate solution, aqueous sodium sulfite solution, aqueous sodium hydrogen carbonate solution
  4. customAfter removing the solvent
  5. customby evaporation
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-79939989016f4a7e8e36cb4cfdc8070f
Source dataset
uspto-grants-1981_08
Patent number
US04282372

Reaction notes

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