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Sodium Hydroxide → 2-Fluoro-4-(8,8-dimethl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl-ethynyl)-benzoic Acid

HRID 24068
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 24068
C([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)=[CH:7][C:6]=1[F:26])C.[OH-].[Na+]>C(O)C.CO.O1CCCC1>[F:26][C:6]1[CH:7]=[C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[CH2:18][CH2:17][C:16]([CH3:25])([CH3:24])[C:15]=3[CH:14]=2)[CH:9]=[CH:10][C:5]=1[C:4]([OH:27])=[O:3]
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Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 129717122-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid ethyl ester2×

Produkt 1

HCID 99675692-Fluoro-4-(8,8-dimethl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl-ethynyl)-benzoic AcidAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel
HCID 887
Methanol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)benzoic acid ethyl ester (Compound 9, 0.1 g, 0.274 mmol) in ethanol(4 mL), methanol (2 mL) and tetrahydrofuran (2 mL) was treated with 1M aqueous sodium hydroxide solution and heated at 70° C. for 1 h. The volatiles were distilled off in vacuo and the residue was diluted with water and dilute hydrochloric acid and extracted with ethyl acetate (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a solid that was recrystallized from hot aqueous acetonitrile to afford the title compound (0.025 g, 27%).

Aufarbeitung

  1. distillationThe volatiles were distilled off in vacuo
  2. additionthe residue was diluted with water and dilute hydrochloric acid
  3. extractionextracted with ethyl acetate (×2)
  4. extractionThe combined organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a solid
  9. customthat was recrystallized from hot aqueous acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-4aa5c292e7b14860b96d1f7ddc13d33a
Quelldatensatz
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06855512B2

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