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Ethyl trifluoroacetate → 1,1,1-Trifluoro-4-hydroxy-4-phenanthren-2-yl-but-3-en-2-one

HRID 1665232
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1665232
[H-].[Na+].[F:3][C:4]([F:11])([F:10])[C:5]([O:7]CC)=O.[C:12]([C:15]1[CH:28]=[CH:27][C:26]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]=2[CH:16]=1)(=[O:14])[CH3:13]>O1CCCC1>[F:11][C:4]([F:3])([F:10])[C:5](=[O:7])[CH:13]=[C:12]([OH:14])[C:15]1[CH:28]=[CH:27][C:26]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]=2[CH:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydrideHCID 80060Methyl 2-phenanthryl ketone

Produkt 1

HCID 766150871,1,1-Trifluoro-4-hydroxy-4-phenanthren-2-yl-but-3-en-2-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a suspension of sodium hydride (NaH; 0.13 g, 5.4 mmol) in 5 mL of anhydrous tetrahydrofuran (THF) was added ethyl trifluoracetate (CF3COOEt; 0.64 g, 4.5 mmol) under argon. After stirring at 25° C. for 10 minutes, 2-acetylphenanthrene (1 g, 4.5 mmol) in 5 mL of THF was added dropwise to the solution. The mixture became clear and orange-hued within 30 minutes, and after stirring for an additional 2 hours, was concentrated under vacuum. The residue was suspended in water, and extracted with ethyl acetate (15 mL) twice. The organic phase was separated, dried over sodium sulfate, and concentrated to dryness under vacuum to give the product (yellow solid; 1.29 g, 90% yield). The product was used directly without further purification.

Aufarbeitung

  1. waitThe mixture became clear and orange-hued within 30 minutes
  2. stirringafter stirring for an additional 2 hours
  3. concentrationwas concentrated under vacuum
  4. extractionextracted with ethyl acetate (15 mL) twice
  5. customThe organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness under vacuum
  8. customto give the product (yellow solid; 1.29 g, 90% yield)
  9. customThe product was used directly without further purification

Quellen und Nachweise

ORD-Eintrag
ord-39a0e09ae8c940cf901f4fcbbacda151
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08039502B2

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