Reaktion #6245

Reaktionsgleichung

Sodium borohydride

4-(3-phthalimidopropyloxy)pyridine

→

desired compound

Ausbeute 54.2%

4-[3-(3-hydroxyisoindolin-1-on-2-yl)propyloxy]pyridine

Ausbeute 54.2%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONAfter the solvent was distilled off
2. 2
   workup.ADDITIONbrine was added to the residue
3. 3
   ExtraktionThe mixture was extracted with chloroform
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off
6. 6
   SonstigeThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10)
7. 7
   Sonstigerecrystallized from ethyl acetate

Vorschrift

Sodium borohydride [1.89 g (50 mmol)] was added to a solution of 2.82 g (10.0 mmol) of 4-(3-phthalimidopropyloxy)pyridine in 150 ml of ethanol. The mixture was stirred at room temperature for 15 minutes. After the solvent was distilled off, brine was added to the residue. The mixture was extracted with chloroform and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10), and then recrystallized from ethyl acetate to obtain 1.54 g of the desired compound (yield: 54.2%, colroless crystals).

Quelle