Triethylamine → Methyl 2-((trimethylsilyl)ethynyl)benzoate

HRID 424795

Reaktionsgleichung

Reaktionsgleichung von HRID 424795
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1I.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 69132Benzoic acid, 2-iodo-, methyl ester

Produkt 1

HCID 11053512Methyl 2-((trimethylsilyl)ethynyl)benzoateAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-iodo-benzoic acid methyl ester (792 mg, 3.02 mmol) in DMF (10 mL) are added trimethylsilylacetylene (854 μL, 6.04 mmol) and triethylamine (2.95 mL, 21.1 mmol). The reaction mixture is degassed for 20 minutes with a stream of nitrogen. Dichloro(bistriphenylphosphene) palladium (II) (212 mg, 0.302 mmol, 10 mol %) and copper (I) iodide (58 mg, 0.302 mmol, 10 mol %) are added and the reaction is heated to 80° C. After 3 h, the reaction is concentrated and the residue is chromatographed eluting with 0 to 5% EtOAc/Hexanes to yield the title compound (597 mg, 85%). GC/MS: 232.

Aufarbeitung

  1. customThe reaction mixture is degassed for 20 minutes with a stream of nitrogen
  2. concentrationthe reaction is concentrated
  3. customthe residue is chromatographed
  4. washeluting with 0 to 5% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b3cb5dace8cb4b3cb449666ab2002aaa
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106077B2

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