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

HRID 1623241Notes

Reaction equation

HRID 1623241 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-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2,6-dimethyl-4H-pyran-4-one (2 g, 16.1 mmol) in 20 ml ethanol was stirred over 10% Pd/C (0.2 g) under hydrogen (15 psi) for 16 hours at ambient temperature. TLC showed two spots; one was desired product and second one was side product in a 1:1 ratio. GCMS M+128 for product, and M+130 for side product.

Sources & evidence

ORD record
ord-0b5216303289407b8086e2e31bbc99e2
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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