3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde → 3-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionaldehyde
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20])[CH:6]=[CH:7][CH:8]=[O:9]>[C].[Pd].O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][CH:8]=[O:9])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of 3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde (5.6 g), palladium-carbon (5%, 0.5 g) and tetrahydrofuran (THF) (160 ml) was subjected to catalytic hydrogenation at room temperature under 1 atmospheric pressure. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate -hexane (1:1), was obtained 3-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionaldehyde, which was recrystallized from ethyl acetate-hexane to give colorless needles, m.p.80-81° C.
Aufarbeitung
- customwas subjected to catalytic hydrogenation at room temperature under 1 atmospheric pressure
- filtrationThe catalyst was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- washFrom the fraction eluted with ethyl acetate -hexane (1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-19a3097309ed41babb10be80c4735499
- Quelldatensatz
- uspto-grants-1999_08
- Patentnummer
- US05932601
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