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

HRID 714153

Reaktionsgleichung

Reaktionsgleichung von HRID 714153
[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-cc1e19f15f044e5bb5bcd6fe17eb0b50
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187397B2

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