Potassium Carbonate → 1-Ethynyl-3-(trifluoromethyl)benzene

HRID 508828

Reaktionsgleichung

Reaktionsgleichung von HRID 508828
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=1)#[CH:3]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 42818851-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzene

Produkt 1

HCID 27784901-Ethynyl-3-(trifluoromethyl)benzeneAusbeute 142,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of trimethyl((3-(trifluoromethyl)phenyl)ethynyl)silane (0.500 g, 2.06 mmol) in ethanol (10 mL) was added potassium carbonate (0.253 g, 1.8 mmol) and the reaction mixture was stirred at RT for 18 h. The reaction mass was quenched in water, neutralized with dil. HCl and extracted with hexane and concentrated to afford 0.200 g of the crude product which was further purified by column chromatography using silica (60-120 mesh) eluting with pet. ether to afford 0.500 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 4.41 (s, 1H), 7.64 (d, J=7.5 Hz, 1H), 7.77-7.81 (m, 3H).

Aufarbeitung

  1. customThe reaction mass was quenched in water
  2. extractionextracted with hexane
  3. concentrationconcentrated
  4. customto afford 0.200 g of the crude product which
  5. customwas further purified by column chromatography
  6. washeluting with pet. ether

Quellen und Nachweise

ORD-Eintrag
ord-d9c25503165c4bbf86de75c231c59820
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096545B2

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