Reaktion #2130187

Reaktionsgleichung

methyl 2-(4-iodophenyl)cyclopropanecarboxylate

2-(di-tert-butylphosphino)-1-phenylindole

trimethylsilylacetylene

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title compound

Methyl 2-(4-((trimethylsilyl)ethynyl)phenyl)cyclopropanecarboxylate

Lösungsmittel

tetramethylethylenediamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was evacuated
2. 2
   Sonstigewas elevated to 80° C
3. 3
   SonstigeAfter consumption of the starting material
4. 4
   Sonstigequenched with water
5. 5
   Extraktionextracted with EtOAc (3×)
6. 6
   WaschenThe combined extracts were washed with brine
7. 7
   Trocknendried over MgSO4
8. 8
   Einengenconcentrated under vacuum
9. 9
   Sonstigea fraction of the residue was purified by flash chromatography
10. 10
    Sonstigeto give 580 mg (40%)
11. 11
    Sonstigeafter purification by flash chromatography (SiO2, EtOAc:PE, 1:8)

Vorschrift

The title compound was prepared from and according to the general procedure A dry Schlenk flask was charged with methyl 2-(4-iodophenyl)cyclopropanecarboxylate (1.66 g, 5.49 mmol), Na2[PdCl4] (18 mg, 0.06 mmol), 2-(di-tert-butylphosphino)-1-phenylindole (37 mg, 0.11 mmol), CuI (21 mg, 0.11 mmol), and tetramethylethylenediamine (10 mL). The mixture was evacuated and backfilled with Ar (3×), and heated to 70° C. before addition of trimethylsilylacetylene (1.4 mL, 10.8 mmol) through the septum and the temperature was elevated to 80° C. After consumption of the starting material indicated by HPLC, the reaction mixture was cooled to room temperature, quenched with water and extracted with EtOAc (3×). The combined extracts were washed with brine, dried over MgSO4 and concentrated under vacuum and a fraction of the residue was purified by flash chromatography to give 580 mg (40%) after purification by flash chromatography (SiO2, EtOAc:PE, 1:8): Rt: 14.56 min (HPLC method I).

Quelle