Ethyl Acetate → Methyl-3-oxo-6,8-dioxabicyclo[3.2.1]octane

HRID 2379170Notes

Reaction equation

HRID 2379170 reaction equation
C([O:8][CH2:9][CH:10]1[O:15][C:14](C)=[CH:13][C:12](=[O:17])[CH2:11]1)C1C=CC=CC=1.[CH3:18]COC(C)=O>[Pd]>[CH3:18][C:10]12[O:15][CH:14]([O:8][CH2:9]1)[CH2:13][C:12](=[O:17])[CH2:11]2

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 199330426-Benzyloxymethyl-2-methyl-5,6-dihydro-4H-pyran-4-one

Product 1

HCID 86748227Methyl-3-oxo-6,8-dioxabicyclo[3.2.1]octaneYield 30%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 4.4 g of the 6-Benzyloxy compound from Step 2 in EtOAc was hydrogenated with H2 and Pd/C (10%). After completion, the reaction was filtrated on a bed of celite and then evaporated to dryness. The cru syrup was then taken up in CH2Cl2 containing 1 g of camphor sulphonic acid. The reaction was stirred at r.t. overnight, filtered and evaporated. Purification by flash chromatography (30% Et2O/pentane) gave 780 mg of the title compound (30%).

Workup

  1. filtrationAfter completion, the reaction was filtrated on a bed of celite
  2. customevaporated to dryness
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography (30% Et2O/pentane)

Sources & evidence

ORD record
ord-eda2a644de254dfdb94eda29ec056675
Source dataset
uspto-grants-1994_11
Patent number
US05360815

Reaction notes

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