2-Phenoxymethyl-2,3-dihydropyran-4-one → 2-Phenoxymethyltetrahydropyran-4-one

HRID 397824Notes

Reaction equation

HRID 397824 reaction equation
[O:1]([CH2:8][CH:9]1[CH2:14][C:13](=[O:15])[CH:12]=[CH:11][O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[O:1]([CH2:8][CH:9]1[CH2:14][C:13](=[O:15])[CH2:12][CH2:11][O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 230012662-Phenoxymethyl-2,3-dihydropyran-4-one

Product 1

HCID 230012782-Phenoxymethyltetrahydropyran-4-oneYield 58.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Phenoxymethyl-2,3-dihydropyran-4-one (2.30 g, 11.3 mmol) was dissolved in ethyl acetate (150 ml). 10% Palladium on charcoal (400 mg) was added. The reaction mixture was hydrogenated until the reaction stopped. The catalyst was removed by filtration through a glas-filter. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (200 g), using ethyl acetate/heptane 1:1 as eluent, to give 1.36 g of 2-phenoxymethyltetrahydropyran-4-one.

Workup

  1. customThe catalyst was removed by filtration through a glas-filter
  2. customThe solvent was removed in vacuo
  3. customThe crude product was purified by flash chromatography on silica (200 g)

Sources & evidence

ORD record
ord-694cc29d925b4de8b77004e2ebb59ba3
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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