Reaktion #6254

Reaktionsgleichung

ethanol ethyl acetate

4-(3-phthalimidopropylthio)pyridine

sodium borohydride

→

desired compound

Ausbeute 54.4%

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

Ausbeute 54.4%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThe solvent was distilled off
2. 2
   workup.ADDITIONsaturated saline was added to the residue
3. 3
   ExtraktionThe mixture was extracted with chloroform
4. 4
   Trocknenthe extract was dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   Sonstigethe residue was purified by column chromatography (eluent

Vorschrift

To a solution of 5.97 g (20.0 mmol) of 4-(3-phthalimidopropylthio)pyridine in 300 ml of ethanol, 1.51 g (40 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 5 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chloroform and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethanol/ethyl acetate =1:10 to give 3.27 g of the desired compound (54.4% yield, colorless crystals), mp. 132°-134° C. NMR (200 MHz, CDCl3) δ: 2.11 (2H, m), 2.97 (2H, m), 3.72 (2H, m), 5.83 (1H, s), 6.98 (2H, d, J=5.4 Hz), 7.47-7.67 (3H, m), 7.77 (1H, dd, J=7.6, 1.2 Hz), 8.02 (2H, m).

Quelle