Reaktion #57537

Reaktionsgleichung

(6-Bromo-pyridin-2-yl)-methanol

phthalimide

triphenylphosphine

1,1-(azodicarbonyl)-dipiperidine

→

2-(6-Bromo-pyridin-2-ylmethyl)-isoindole-1,3-dione

Ausbeute 80.4%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to 0° C.
2. 2
   Sonstigethe resulting precipitate was removed via filtration
3. 3
   workup.ADDITIONA saturated aqueous sodium bicarbonate solution was added to the filtrate
4. 4
   Extraktionthe solution was extracted several times with ethyl acetate
5. 5
   TrocknenThe combined organic extracts were dried over magnesium sulfate and condensed under reduced pressure
6. 6
   SonstigeThe crude residue was purified by column chromatography with a gradient of 10 to 75% AcOEt/hexanes

Vorschrift

(6-Bromo-pyridin-2-yl)-methanol (2949 mg, 15.68 mmol), phthalimide (3000 mg, 20.39 mmol), triphenylphosphine (5348 mg, 20.39 mmol) and 1,1-(azodicarbonyl)-dipiperidine) 5144, 20.39 mmol) were dissolved in THF (150 mL) and stirred at room temperature for 4 h. The reaction mixture was cooled to 0° C. and the resulting precipitate was removed via filtration. A saturated aqueous sodium bicarbonate solution was added to the filtrate and the solution was extracted several times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and condensed under reduced pressure. The crude residue was purified by column chromatography with a gradient of 10 to 75% AcOEt/hexanes to give 2-(6-Bromo-pyridin-2-ylmethyl)-isoindole-1,3-dione as a white solid (4000 mg, 80%) MS ES (MH+317.2/319.1).

Quelle