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Triethylamine → 7-(4-Fluorophenyl)-7-(1-hydroxy-2-naphthyl)heptanoic acid

HRID 373373
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 373373
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([CH:13]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:3]=1.C(N(CC)CC)C>CO.[C].[Pd]>[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH:13]([C:4]2[CH:3]=[CH:2][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[OH:12])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:27][CH:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 8471TriethylamineHCID 145139627-(4-Bromo-1-hydroxy-2-naphthyl)-7-(4-fluorophenyl)heptanoic acid

Produkt 1

HCID 145139657-(4-Fluorophenyl)-7-(1-hydroxy-2-naphthyl)heptanoic acidAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887Methanol
Lösungsmittel

Versuchsvorschrift

To a solution of 7-(4-bromo-1-hydroxy-2-naphthyl)-7-(4-fluorophenyl)heptanoic acid (1.70 g) in methanol (10 ml) were added 5% palladium-carbon (200 mg) and triethylamine (0.53 ml) and hydrogenation was carried out at room temperature for 1.5 hours. The catalyst was filtered off and the filtrate was distilled off at reduced pressure. The residue was extracted by addition of ethyl acetate and water. The ethyl acetate layer was washed with saturated saline and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by subjecting it to silica gel chromatography and eluting with ethyl acetate/hexane (1:2) to obtain 7-(4-fluorophenyl)-7-(1-hydroxy-2-naphthyl)heptanoic acid (930 mg) (Compound B-3). The physical properties and NMR spectrum data thereof are shown in Table 2.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. distillationthe filtrate was distilled off at reduced pressure
  3. extractionThe residue was extracted by addition of ethyl acetate and water
  4. washThe ethyl acetate layer was washed with saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified
  8. washeluting with ethyl acetate/hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-9b25ba72802443a1b086186fe2324350
Quelldatensatz
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05162571

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