Methanol → HCID 15296555, Verbindung

HRID 2210074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2210074
C1(C[O:8][C:9]2[CH:19]=[CH:18][C:12]3[C:13](=[O:17])[CH:14]=[CH:15][O:16][C:11]=3[C:10]=2[CH2:20]/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)C=CC=CC=1.CO.[H][H]>[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:19]=[CH:18][C:12]2[C:13](=[O:17])[CH2:14][CH2:15][O:16][C:11]=2[C:10]=1[CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 19379910(E)-7-(Phenylmethoxy)-8-(3-phenyl-2-propenyl)-4H-1-benzopyran-4-oneHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 15296555HCID 15296555, VerbindungAusbeute 228,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 6.1 g (16.6 mmol) of (E)-7-(phenylmethoxy)-8-(3-phenyl-2-propenyl)-4H-1-benzopyran-4-one from the preceding example, 1 g of 10% palladium on carbon, 100 mL of methanol, and 300 mL of ethyl acetate was stirred at room temperature, in an atmosphere of hydrogen until approximately one third of the theoretical volume of hydrogen gas was taken up. The catalyst was filtered with suction and the filtrate concentrated in vacuo. The residue was dissolved in 150 mL of methanol and 0.5 g of Raney nickel was added. The hydrogenation was continued with careful monitoring by TLC analysis. When the reduction was essentially complete, the catalyst was filtered with suction and the filtrate concentrated in vacuo. The solid residue (4.75 g) was combined with 6.4 g from another experiment (23.9 mmol scale) and chromatographed on silica gel. Elution with hexane-ethyl acetate mixtures afforded 10.73 g (93.9%) of the title compound as a colorless solid, mp 110°-112° C.

Aufarbeitung

  1. filtrationThe catalyst was filtered with suction
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in 150 mL of methanol
  4. addition0.5 g of Raney nickel was added
  5. filtrationthe catalyst was filtered with suction
  6. concentrationthe filtrate concentrated in vacuo
  7. customchromatographed on silica gel
  8. washElution with hexane-ethyl acetate mixtures

Quellen und Nachweise

ORD-Eintrag
ord-9e820fffd8424a9aa16ab3dd7e94aa13
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05457124

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