4-Benzoyldihydro-3H-furan-2-one → Dihydro-4-(phenylmethyl)-2(3H)-furanone

HRID 8195

Reaktionsgleichung

Reaktionsgleichung von HRID 8195
[C:1]([CH:9]1[CH2:13][O:12][C:11](=[O:14])[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd](Cl)Cl>[CH2:1]([CH:9]1[CH2:13][O:12][C:11](=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 2297594-Benzoyldihydro-3H-furan-2-one

Produkt 1

HCID 5150640Dihydro-4-(phenylmethyl)-2(3H)-furanoneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-benzoyl-dihydro-furan-2-one (5 g) in methanol (250 mL) in a Parr® reactor is added palladium chloride (0.25 g). The mixture is shaken under hydrogen (50 PSI) for 3 h. The mixture is filtered through a pad of Celite® (40 g) and the filtrate concentrated. The residue is chromatographed on SiO2 (10% ethyl acetate/hexanes, then 30% ethyl acetate/hexanes) to yield the title compound, (2.5 g, 34% from 3-benzoylpropionic acid), as a colorless liquid.

Aufarbeitung

  1. filtrationThe mixture is filtered through a pad of Celite® (40 g)
  2. concentrationthe filtrate concentrated
  3. customThe residue is chromatographed on SiO2 (10% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8b00c056f9bc46b2b56d079b375aa7cc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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