Trimethylsilylacetylene → 2,2,4,4-Tetramethyl-7-trimethylsilylethynyl-chroman

HRID 2226117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226117
[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6](Br)=[CH:7][CH:8]=2)[O:3]1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:7][CH:8]=2)[O:3]1

Komponenten

5

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 18965395HCID 18965395, Verbindung2×

Produkt 1

HCID 189663522,2,4,4-Tetramethyl-7-trimethylsilylethynyl-chroman

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 2 g (7.4 mmol) of 2,2,4,4 tetramethyl-7-bromochroman (Compound 42) and 3.63 g (37.0 mmol) of trimethylsilylacetylene in 5 ml of triethylamine was placed in a heavy walled glass tube and degassed under nitrogen. The mixture was then treated, under nitrogen, with 130 mg (0.6826 mmol) of cuprous iodide and 260 mg (0.3704 mmol) of bis (triphenyl phosphine) palladium (II) chloride. The reaction mixture was degassed again and placed under nitrogen and the tube was sealed. The mixture was heated to 60 degrees C. for 24 hours and then cooled to room temperature and filtered through celite. The solvent was removed in vacuo and the residue purified by flash column chromatography (silica; 2% ethyl acetate/hexane) to give the title compound as a pale yellow solid.

Aufarbeitung

  1. customdegassed under nitrogen
  2. customThe reaction mixture was degassed again
  3. customthe tube was sealed
  4. temperaturecooled to room temperature
  5. filtrationfiltered through celite
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by flash column chromatography (silica; 2% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-952368d81c944e21929a71ff0ea79403
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05346895

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