5-[(Benzyloxy)methyl]-4-hydroxyfuran-2(5H)-one → 4-hydroxy-5-hydroxymethylfuran-2(5H)-one

HRID 552915Notes

Reaction equation

HRID 552915 reaction equation
C([O:8][CH2:9][CH:10]1[O:14][C:13](=[O:15])[CH:12]=[C:11]1[OH:16])C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[OH:16][C:11]1[CH:10]([CH2:9][OH:8])[O:14][C:13](=[O:15])[CH:12]=1

Participants

5

Reactant 2

HCID 547140145-[(Benzyloxy)methyl]-4-hydroxyfuran-2(5H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 671646764-hydroxy-5-hydroxymethylfuran-2(5H)-oneYield 94.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

386.0 mg (1.75 mmol) of 5-benzyloxymethyl-4-hydroxyfuran-2(5H)-one (Aragon, D. T. et al., J. Org. Chem. 68, 3363-3365, 2003) are initially charged in 19.3 ml of ethanol, 38.6 mg (0.27 mmol) of Pd(OH)2/C (20%) are added and the mixture is hydrogenated at room temperature until the hydrogen uptake has stopped. Removal of the catalyst by filtration and evaporation of the solvent gives 216 mg (94.7% of theory) of 4-hydroxy-5-hydroxymethylfuran-2(5H)-one which can be used without further purification for a subsequent reaction.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-daeb4a1fcf7d45f794bd2cf128dd66b0
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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