2,6-Dimethyl-4-pyranone → Tetrahydro-2,6-dimethyl-4H-pyran-4-one

HRID 2379164Notes

Reaction equation

HRID 2379164 reaction equation
[CH3:1][C:2]1[O:8][C:7]([CH3:9])=[CH:6][C:4](=[O:5])[CH:3]=1>CCO>[CH3:9][CH:7]1[CH2:6][C:4](=[O:5])[CH2:3][CH:2]([CH3:1])[O:8]1

Participants

3

Reactant 1

HCID 138622,6-Dimethyl-4-pyranone

Product 1

HCID 70626Tetrahydro-2,6-dimethyl-4H-pyran-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,6-dimethyl-γ-pyrone (17 g, Aldrich) in EtOH 95% (300 mL) was hydrogenated for 3 days under 70 psi. After filtration over celite, the solvent was evaporated and replaced by CH2Cl2. The solution was then treated with celite (30 g) and PCC (48.5 g). The suspension was stirred for 3 hr. and the reaction was diluted with Et2O (300 mL) and then filtered over a pad of celite. The filtrate was evaporated to dryness and the residual solution was then chromatographed using hexane/Et2O (1:1) to give the title compound.

Workup

  1. filtrationAfter filtration over celite
  2. customthe solvent was evaporated
  3. additionThe solution was then treated with celite (30 g) and PCC (48.5 g)
  4. additionand the reaction was diluted with Et2O (300 mL)
  5. filtrationfiltered over a pad of celite
  6. customThe filtrate was evaporated to dryness
  7. customthe residual solution was then chromatographed

Sources & evidence

ORD record
ord-1df962bf512b43138b45ea669371bff7
Source dataset
uspto-grants-1994_11
Patent number
US05360815

Reaction notes

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