Trimethylsilylacetylene → HCID 15021947, Verbindung

HRID 466513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466513
[CH2:1]([C:3]12[CH2:10][O:9][C:6]([C:11]3[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=3)([O:7][CH2:8]1)[O:5][CH2:4]2)[CH3:2].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>C(NCC)C>[CH2:1]([C:3]12[CH2:10][O:9][C:6]([C:11]3[CH:16]=[CH:15][C:14]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[CH:13][CH:12]=3)([O:7][CH2:8]1)[O:5][CH2:4]2)[CH3:2]

Komponenten

4

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 150219464-Ethyl-1-(4-iodophenyl)-2,6,7-trioxabicyclo[2,2,2]octane

Produkt 1

HCID 15021947HCID 15021947, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

Bis-triphenylphosphine palladium dichloride (60 mg) and cuprous iodide (10 mg) were added to a stirred solution of 4-ethyl-1-(4-iodophenyl)-2,6,7-trioxabicyclo[2,2,2]octane (1.5 gms) and trimethylsilylacetylene (0.92 ml) in dry diethylamine (40 ml) under nitrogen. The resulting mixture was stirred at room temperature for 16 hours. After this time the solvent was removed under vacuum and the residue extracted with diethylether. The ethereal solution was washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by column chromatography on alumina, eluting with 30% dichloromethane in hexane saturated with ammonia. 4-Ethyl-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo[2,2,2]octane (1.2 gms) was obtained as an off-white solid (1.2 gms) after recrystallisation from hexane.

Aufarbeitung

  1. customAfter this time the solvent was removed under vacuum
  2. extractionthe residue extracted with diethylether
  3. washThe ethereal solution was washed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on alumina
  7. washeluting with 30% dichloromethane in hexane saturated with ammonia

Quellen und Nachweise

ORD-Eintrag
ord-54da0ad793dd4e11969a6e84bb943a7e
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157029

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