methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl)propanoate → methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-8-propyl-2H-1-benzopyran-2-yl)propanoate

HRID 978747

Reaktionsgleichung

Reaktionsgleichung von HRID 978747
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=O)[CH2:7][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])([CH3:10])[O:9][C:4]=2[C:3]=1[CH2:20][CH2:21][CH3:22]>C(O)(=O)C.CO.[Pd]>[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH2:7][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])([CH3:10])[O:9][C:4]=2[C:3]=1[CH2:20][CH2:21][CH3:22]

Komponenten

5

Edukt 1

HCID 2801556methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl)propanoate

Produkt 1

HCID 14882982methyl 3-(3,4-dihydro-7-hydroxy-2-methyl-8-propyl-2H-1-benzopyran-2-yl)propanoateAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4.1 g (13.4 mmole) of ester product of Example 4 in 100 ml of acetic acid and 50 ml of methanol was hydrogenated for 21 hours at 4 psi and room temperature using palladium on carbon as catalyst. The catalyst was filtered and the filtrate was evaporated to dryness. Chromatography of the residue on silica gel using 20% ethyl acetate/hexane as eluent gave 1.8 g of the title compound as an oil. Structure assignment was confirmed by nmr and infrared spectra.

Aufarbeitung

  1. filtrationThe catalyst was filtered
  2. customthe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b92a34b9b563428581798fe046ba4de7
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04665203

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