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4-[3,5,6-Trimethyl-1,4-benzoquinon-2-yl(3-pyridyl)methyl]-alpha-methylcinnamic acid → 3-(4-[3,5,6-Trimethyl-1,4-benzoquinon-2-yl-(3-pyridyl)methyl]phenyl)propionic acid

HRID 232059
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 232059
[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[C:13]1[CH:24]=[CH:23][C:16]([CH:17]=[C:18](C)[C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1>C(O)(=O)C.[Pd].[C]>[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[C:13]1[CH:24]=[CH:23][C:16]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 571128964-[3,5,6-Trimethyl-1,4-benzoquinon-2-yl(3-pyridyl)methyl]-alpha-methylcinnamic acid

Produkt 1

HCID 142777693-(4-[3,5,6-Trimethyl-1,4-benzoquinon-2-yl-(3-pyridyl)methyl]phenyl)propionic acidAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

4-[3,5,6-trimethyl-1,4-benzoquinon-2-yl-(3-pyridyl)methyl]-α-methylcinnamic acid, 0.7 g (1.75 mmol), was hydrogenated with 0.2 g of 5% Pd-carbon in 6 ml of acetic acid (the reaction completed in about 2 hours). The catalyst was filtered off, and the filtrate was concentrated, to which water was added and neutralized with a saturated aqueous solution of sodium hydrogen carbonate. The resultant substance was extracted with ethyl acetate, and oxidized by shaking with an aqueous solution of ferric chloride. After the organic phase was washed with water and dried, the solvent was evaporated off and the residue was purified with silica gel column chromatography (ethyl acetate-ethanol (9:1)) and recrystallized from ethyl acetate, to give 0.3 g (44.2%) of 3-(4-[3,5,6-trimethyl-1,4-benzoquinon-2-yl-(3-pyridyl)methyl]phenyl)propionic acid. The physical data are shown in Table 1.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated, to which water
  3. additionwas added
  4. extractionThe resultant substance was extracted with ethyl acetate
  5. washAfter the organic phase was washed with water
  6. customdried
  7. customthe solvent was evaporated off
  8. customthe residue was purified with silica gel column chromatography (ethyl acetate-ethanol (9:1))
  9. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-00ba0090a69e4f41b6dbc23c038ec01e
Quelldatensatz
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04851413

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