3-Methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester → 3-Methyl-4-ethylbenzofuran-2-carboxylic acid ethyl ester

HRID 29321

Reaktionsgleichung

Reaktionsgleichung von HRID 29321
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[CH2:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH3:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 687131603-Methyl-4-vinylbenzofuran-2-carboxylic acid ethyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 687161913-Methyl-4-ethylbenzofuran-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.40 g (1.74 mmol) of 3-methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester in 25 mL of ethyl acetate under nitrogen was added 0.050 g of 10% palladium on carbon. The reaction was shaken on a Parr hydrogenator under 40 psi of hydrogen for 4 h. The reaction was then filtered through a pad of celite. The celite was washed with an additional 150 mL of ethyl acetate and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:30) to provide 0.395 of 3-methyl-4-ethylbenzofuran-2-carboxylic acid ethyl ester.

Aufarbeitung

  1. filtrationThe reaction was then filtered through a pad of celite
  2. washThe celite was washed with an additional 150 mL of ethyl acetate
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:30)

Quellen und Nachweise

ORD-Eintrag
ord-303617bd87414db3b92775e9bb5c64c9
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420001B2

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