2,4-Pentanedione, 3-(phenylmethylene)- → 2,4-Pentanedione, 3-benzyl-

HRID 77638

Reaktionsgleichung

Reaktionsgleichung von HRID 77638
[CH:1](=[C:8]([C:12](=[O:14])[CH3:13])[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[CH2:1]([CH:8]([C:9](=[O:11])[CH3:10])[C:12](=[O:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 957822,4-Pentanedione, 3-(phenylmethylene)-

Produkt 1

HCID 977572,4-Pentanedione, 3-benzyl-Ausbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-Benzylidene-2,4-pentanedione (7, 6.50 g, 34.5 mmol) and palladium on activated carbon (0.25 g, 10%) were combined in ethyl acetate (50 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 4 hr at room temperature. The resulting mixture was filtered through celite and the solvent evaporated to afford an oil. The crude oil was distilled bulb to bulb to give 6.52 g (99%) of a clear oil; 1H NMR: δ enol form: 2.02 (s, 6H), 3.62 (s, 2H), 7.24 (m, 5H); keto form: 2.07 (s, 6H), 3.11 (d, 2H, J=7.4 Hz), 4.01 (t, 1H, J=7.7 Hz), 7.24 (m, 5H); 13C NMR: δ 22.9, 29.4, 32.5, 33.8, 69.2, 107.9, 125.9, 126.3, 127.0, 128.1, 128.2, 137.7, 139.3, 191.4, 202.9.

Aufarbeitung

  1. customfor 4 hr
  2. customat room temperature
  3. filtrationThe resulting mixture was filtered through celite
  4. customthe solvent evaporated
  5. customto afford an oil
  6. distillationThe crude oil was distilled bulb to bulb

Quellen und Nachweise

ORD-Eintrag
ord-235062ebc7fd4f89a3a0b013ce91f227
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841326B2

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