6-Benzyloxymethyl-2-methyl-5,6-dihydro-4H-pyran-4-one → 5-Methyl-3-oxo-6,8-dioxabicyclo[3.2.1]octane

HRID 21567Notes

Reaction equation

HRID 21567 reaction equation
C([O:8][CH2:9][CH:10]1[O:15][C:14]([CH3:16])=[CH:13][C:12](=[O:17])[CH2:11]1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH3:16][C:14]12[O:15][CH:10]([CH2:9][O:8]1)[CH2:11][C:12](=[O:17])[CH2:13]2

Participants

4

Reactant 1

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

Product 1

HCID 189580315-Methyl-3-oxo-6,8-dioxabicyclo[3.2.1]octaneYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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 filtered on a bed of celite and then evaporated to dryness. The cru syrup was then taken up in CH2C2 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 filtered on a bed of celite
  2. customevaporated to dryness
  3. additioncontaining 1 g of camphor sulphonic acid
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (30% Et2O/pentane)

Sources & evidence

ORD record
ord-a8540259f1b447dfae054082c2ce8dfe
Source dataset
uspto-grants-1995_06
Patent number
US05424320

Reaction notes

Loading…