Potassium Carbonate → 6-Ethynylisoquinoline

HRID 598840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598840
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[N:10][CH:9]=[CH:8]2.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O.O>[C:4]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[N:10][CH:9]=[CH:8]2)#[CH:3]

Komponenten

6

Edukt 2

HCID 11430Potassium CarbonateHCID 579505646-((Trimethylsilyl)ethynyl)isoquinoline

Produkt 1

HCID 579505416-EthynylisoquinolineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-(2-(trimethylsilyl)ethynyl)isoquinoline (2.2 g, 9.8 mmol) in 45 mL of MeOH was added potassium carbonate (2.7 g, 20 mmol). After 1 hour, the reaction mixture was diluted with 100 mL of EtOAc and 50 mL of water. The mixture was partitioned and the aqueous portion was extracted three times with 50 mL of EtOAc. The combined organic layers were washed with 100 mL of brine and dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (5% to 30% EtOAc/hexanes) afforded 6-ethynylisoquinoline (1.3 g, 87% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ pp 9.25 (s, 1H), 8.56 (d, J=5.7 Hz, 1H), 7.99 (s, 1H), 7.93 (d, J=8.4 Hz, 1H), 7.65 (dd, J=1.2 Hz, 8.6 Hz, 1H), 7.62 (d, J=5.8 Hz, 1H), 3.26 (s, 1H).

Aufarbeitung

  1. customThe mixture was partitioned
  2. extractionthe aqueous portion was extracted three times with 50 mL of EtOAc
  3. washThe combined organic layers were washed with 100 mL of brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8e18e16dd8e347b98fd2138a50f09876
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897619B2

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