Methyl 5-(chloromethyl)-2-furoate → Methyl 5-methyl-2-furancarboxylate

HRID 612301

Reaktionsgleichung

Reaktionsgleichung von HRID 612301
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1>C(OCC)(=O)C.[Pd]>[CH3:2][C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1

Komponenten

4

Edukt 1

HCID 75065Methyl 5-(chloromethyl)-2-furoate

Produkt 1

HCID 137628Methyl 5-methyl-2-furancarboxylateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl 5-chloromethyl-2-furoate (5.0 g, 28.7 mmol) in ethyl acetate (40 ml) was hydrogenated over 10% palladium on charcoal (50 mg) for 3 h. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were concentrated in vacuo and the residue purified by chromatography on silica gel eluting with 10% ethyl acetate in hexane to yield the title compound as a colourless oil (3.78 g, 94%); νmax (CH2Cl2) 1725, 1534, 1522, 1437 and 1311 cm-1 ; δH (CDCl3, 90 MHz) 2.38 (3 H, s), 3.86 (3 H, s), 6.12 (1 H, br d, J 4 Hz) and 7.07 (1 H, d, J 4 Hz). [Mass spectrum: M+ (140)].

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. customthe residue purified by chromatography on silica gel eluting with 10% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-5c1870501952413eab352dad8fe7b7ce
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06001997

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