4,4-Dimethyl-pent-2-enoic acid methyl ester → 4,4-Dimethyl-pentanoic acid methyl ester

HRID 1783870

Reaktionsgleichung

Reaktionsgleichung von HRID 1783870
[CH3:1][O:2][C:3](=[O:10])[CH:4]=[CH:5][C:6]([CH3:9])([CH3:8])[CH3:7]>CO.C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7]

Komponenten

5

Edukt 1

HCID 5582314,4-Dimethyl-pent-2-enoic acid methyl ester

Produkt 1

HCID 126561444,4-Dimethyl-pentanoic acid methyl esterAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4,4-Dimethyl-pent-2-enoic acid methyl ester (8.52 g, 60.0 mmol) was dissolved in MeOH (30 mL) and ethyl acetate (30 mL). Palladium on carbon (10 wt %) (˜50 mg) was added to the reaction and was placed under a H2 balloon (1 atm). The reaction was allowed to stir for 12 hours, flushed with nitrogen and filtered over a pad of celite. Evaporated to provide 4,4-dimethyl-pentanoic acid methyl ester (7.0 g, 48.5 mmol, 81%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 0.89 (s, 9H), 1.53-1.57 (m, 2H), 2.26-2.30 (m, 2H), 3.67 (s, 3H).

Aufarbeitung

  1. customflushed with nitrogen
  2. filtrationfiltered over a pad of celite
  3. customEvaporated

Quellen und Nachweise

ORD-Eintrag
ord-2c239dc3820e416cbba4e6bf8b0413c1
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501408B2

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