Trimethylsilylacetylene → (4-Tert-butyl-benzyl)-[2-(3-trimethylsilanylethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 19795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19795
[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23](Br)[CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31]>C(N(CC)CC)C.C([O-])(O)=O.[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1)[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])[CH:22]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 68562789HCID 68562789, Verbindung

Produkt 1

HCID 68560300(4-Tert-butyl-benzyl)-[2-(3-trimethylsilanylethynyl-phenyl)-ethyl]-carbamic acid tert-butyl esterAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8471TriethylamineLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of the crude [2-(3-bromo-phenyl)-ethyl]-(4-tert-butyl-benzyl)-carbamic acid tert-butyl ester (515 mg, 1.154 mmol), bis(triphenylphosphine)palladium(II)chloride (32 mg, 0.0461 mmol), CuI (11 mg, 0.0577 mmol) and (trimethylsilyl)acetylene (251 μl, 1.73 mmol) in triethylamine (3.4 ml) was heated in a sealed tube at 105° C. over night. The mixture was then cooled to RT, diluted with sat. NaHCO3-solution and extracted three times with ethyl acetate. The combined ethyl acetate layers were then washed with water and brine and were dried (Na2SO4) and evaporated. The remaining residue was purified by chromatography (heptane/EtOAc 100:0 to 95:5) to obtain the title compound as a yellow gum (441 mg, 82%). MS (ISP) 464.4 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was then cooled to RT
  2. extractionextracted three times with ethyl acetate
  3. washThe combined ethyl acetate layers were then washed with water and brine
  4. dry with materialwere dried (Na2SO4)
  5. customevaporated
  6. customThe remaining residue was purified by chromatography (heptane/EtOAc 100:0 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-8c4a07f24aa3494b88f1f616f709d796
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745477B2

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