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

HRID 552915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552915
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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 671646764-hydroxy-5-hydroxymethylfuran-2(5H)-oneAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-daeb4a1fcf7d45f794bd2cf128dd66b0
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951951B2

Notizen zur Reaktion

Wird geladen…