2-Furanacrylic acid → 3-(Oxolan-2-yl)propanoic acid

HRID 253628

Reaktionsgleichung

Reaktionsgleichung von HRID 253628
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9]>CO.[Pd]>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Komponenten

4

Edukt 1

HCID 6434022-Furanacrylic acid

Produkt 1

HCID 2631613-(Oxolan-2-yl)propanoic acidAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(E)-3-(Furan-2-yl)acrylic acid (10 g, 72.4 mmol) was treated with Pd/C (1 g) in MeOH (100 mL). The mixture was heated at 60° C. at 60 psi under H2 for 12 hrs. After filtering off the catalyst, the filtrate was concentrated to afford 9.8 g (93%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.42-1.56 (m, 1H) 1.77-1.96 (m, 4H) 1.93-2.07 (m, 1H) 2.41-2.56 (m, 2H) 3.71-3.79 (m, 1H) 3.82-3.94 (m, 2H); MS (DCI/NH4+) m/z 145 (M+H)+.

Aufarbeitung

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-c24bd6cde8a1423e82f87555f0a8c26e
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872033B2

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