Water → HCID 69997151, Verbindung

HRID 963430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963430
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4]1)[CH3:2].C([Si:22]([CH3:25])([CH3:24])[CH3:23])#C.O.[CH2:27](N(CC)CC)[CH3:28]>CN(C)C=O.[Cu]I>[CH2:27]([C:2]#[C:1][N:3]1[C:12]2[C:7](=[CH:8][C:9]([Si:22]([CH3:25])([CH3:24])[CH3:23])=[CH:10][CH:11]=2)[C:6](=[O:14])[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4]1)[CH3:28]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 619729HCID 619729, Verbindung

Produkt 1

HCID 69997151HCID 69997151, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of ethyl 1-ethyl-6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate (Example 13h)), 1.94 ml of ethynyltrimethylsilane, 70 mg of bis-trimethylphosphine-palladium dichloride and 2.5 mg of copper(I) iodide in 7 ml of triethylamine and 7 ml of dimethylformamide is stirred at 60° for 9 hrs. After cooling to room temperature the reaction mixture is treated with 100 ml of water and extracted twice with 50 ml of methylene chloride each time. The combined organic phases are washed twice with 250 ml of water each time and once with 250 ml of a saturated, aqueous sodium chloride solution and dried over magnesium sulphate. The crude product is chromatographed on aluminium oxide (neutral, grade III) with n-hexane/ethyl acetate 1:1. 1.27 g (80%) of ethyl 1-ethyl-6-trimethylsilyl-ethynyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate are obtained.

Aufarbeitung

  1. extractionextracted twice with 50 ml of methylene chloride each time
  2. washThe combined organic phases are washed twice with 250 ml of water each time
  3. dry with materialonce with 250 ml of a saturated, aqueous sodium chloride solution and dried over magnesium sulphate
  4. customThe crude product is chromatographed on aluminium oxide (neutral, grade III) with n-hexane/ethyl acetate 1:1

Quellen und Nachweise

ORD-Eintrag
ord-b05545c695d14780a152db0bc7a6d2c2
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763450

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