diethyl 3,4-dihydro-4-oxo-7-hydroxy-8-propyl-2H-1-benzopyran-2,2-dipropanoate → diethyl 3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoate

HRID 2371627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371627
O=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([OH:15])=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:3]1>C(O)(=O)C.[H][H].[Pd]>[CH2:12]([C:11]1[C:6]2[O:5][C:4]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:3][CH2:2][C:7]=2[CH:8]=[CH:9][C:10]=1[OH:15])[CH2:13][CH3:14]

Komponenten

5

Edukt 1

HCID 19756625diethyl 3,4-dihydro-4-oxo-7-hydroxy-8-propyl-2H-1-benzopyran-2,2-dipropanoate

Produkt 1

HCID 15157486diethyl 3,4-dihydro-8-propyl-7-hydroxy-2H-1-benzopyran-2,2-dipropanoateAusbeute 19,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 178418361HCID 178418361, VerbindungKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

The title product of Example 1 (4.19 g, 10.3 mmol) was dissolved in 50 ml of acetic acid, and then hydrogenated at 70° C. using 60 psi of hydrogen and 10% palladium on carbon as catalyst. After eight hours, the mixture was allowed to cool, and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silicagel column. Elution with 20% ethyl acetate/hexane afforded the title compound (0.80 g).

Aufarbeitung

  1. customhydrogenated at 70° C.
  2. temperatureto cool
  3. custominsolubles were removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed on silicagel column
  6. washElution with 20% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-9b633aeee933475fa98baf2bef216144
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05093353

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