StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium ethoxide → 1-{2-hydroxy-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]-2-trifluoromethylpentyl}-1H-quinolin-4-one

HRID 2106032
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2106032
[CH3:1][C:2]([C:12]1[CH:13]=[C:14]([C:18]2([CH3:23])[O:22][CH2:21][CH2:20][O:19]2)[CH:15]=[CH:16][CH:17]=1)([CH3:11])[CH2:3][C:4]1([C:7]([F:10])([F:9])[F:8])[CH2:6][O:5]1.[OH:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][CH:26]=1.[O-]CC.[Na+]>C(O)C>[OH:5][C:4]([C:7]([F:9])([F:8])[F:10])([CH2:3][C:2]([CH3:1])([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2([CH3:23])[O:22][CH2:21][CH2:20][O:19]2)[CH:13]=1)[CH3:11])[CH2:6][N:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25](=[O:24])[CH:26]=[CH:27]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 57810032HCID 57810032, VerbindungHCID 178516385CID 5280925

Produkt 1

HCID 578097811-{2-hydroxy-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]-2-trifluoromethylpentyl}-1H-quinolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 2-{3-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]phenyl}-2-methyl-[1,3]dioxolane (0.514 g, 1.55 mmol), 4-hydroxyquinoline (0.433 g, 2.98 mmol), and sodium ethoxide (21 wt. % solution in ethanol, 0.55 mL, 1.49 mmol) in ethanol (4.2 mL) was heated at 85° C. for 14 hours, cooled to room temperature, quenched with water, and concentrated in vacuo to remove most of the ethanol. The residue was diluted with half saturated aqueous sodium bicarbonate solution and extracted with methylene chloride. The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate-hexanes as the eluent. The product-rich fractions were concentrated in vacuo to afford 1-{2-hydroxy-4-methyl-4-[3-(2-methyl-[1,3]dioxolan-2-yl)phenyl]-2-trifluoromethylpentyl}-1H-quinolin-4-one. Yield: 0.35 g.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customquenched with water
  3. concentrationconcentrated in vacuo
  4. customto remove most of the ethanol
  5. additionThe residue was diluted with half saturated aqueous sodium bicarbonate solution
  6. extractionextracted with methylene chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. concentrationThe product-rich fractions were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-de6df738a4184eb0ab57ba11282ed070
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07579469B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion