2,6-Dimethyl-4-pyranone → (2R,6S)-2,6-dimethyloxan-4-one

HRID 1471106Notes

Reaction equation

HRID 1471106 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1>C(O)C.[Pd]>[CH3:1][C@@H:2]1[CH2:7][C:6](=[O:8])[CH2:5][C@H:4]([CH3:9])[O:3]1

Participants

4

Reactant 1

HCID 138622,6-Dimethyl-4-pyranone

Product 1

HCID 10441716(2R,6S)-2,6-dimethyloxan-4-oneYield 17.43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,6-Dimethyl-4H-pyran-4-one (10 g, 81 mmol) was dissolved in ethanol (125 mL) and Pd/C (1 g, 0.94 mmol) was added. The mixture was hydrogenated in a Parr shaker under H2 (0.325 g, 161 mmol) (70 psi) at room temperature for 12 hrs. The catalyst was filtered through a pad of CELITE® and washed with ethanol. The filtrate was concentrated in vacuum and the residue was purified via BIOTAGE® (2% to 25% EtOAc/Hex; 160 g column). Two fractions of clear oils were isolated. The first eluting one corresponded to (2R,6S)-2,6-dimethyldihydro-2 H-pyran-4(3 H)-one (1.8 g, 14.04 mmol, 17.43% yield) while the second one corresponded to Cap-179, step a (1.8 g).

Workup

  1. filtrationThe catalyst was filtered through a pad of CELITE®
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated in vacuum
  4. customthe residue was purified via BIOTAGE® (2% to 25% EtOAc/Hex; 160 g column)
  5. customTwo fractions of clear oils were isolated
  6. washThe first eluting one

Sources & evidence

ORD record
ord-88c3211b897b4215a22ce678e24ebbdb
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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