1,5-Bis(4-methoxyphenyl)-1,4-pentadien-3-one → HCID 2801509, Verbindung

HRID 1378396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378396
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH:7]=[CH:8][C:9]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:10])=[CH:5][CH:4]=1.[H][H]>C1COCC1.CO.[Pt](=O)=O>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][C:9](=[O:10])[CH2:8][CH2:7][C:6]2[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 2

HCID 1012201,5-Bis(4-methoxyphenyl)-1,4-pentadien-3-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 2801509HCID 2801509, VerbindungAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of commercially available di(4-methoxybenzylidene) acetone (3.5 g, 12 mmol) in THF-MeOH (1:1,100 mL) was added platinum (IV) oxide (90 mg) and the resulting mixture was stirred at room temperature under 4 atmospheres of hydrogen for 19 hours. The catalyst was filtered and washed with THF, and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (hexane-ethyl acetate 3:1) to provide 1,5-bis(4-methoxyphenyl)-3-pentanone (2.13 g) and the reduced side product 1,5-bis(4-methoxyphenyl)-3-pentanol (1.0 g).

Aufarbeitung

  1. filtrationThe catalyst was filtered
  2. washwashed with THF
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (hexane-ethyl acetate 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-05fb986b373f45938dbf6fad166d9702
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668146

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