Reaktion #428687

Reaktionsgleichung

HCl

potassium hydroxide

3-hydroxytetrahydrofuran

6-chloro-nicotinic acid

3-hydroxytetrahydrofuran

potassium hydroxide

→

title compound

6-(Tetrahydro-furan-3-yloxy)-nicotinic acid

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated at 120 C for 24 h
2. 2
   Temperaturthe mixture heated at 120 C for 24 h
3. 3
   Extraktionextracted into EtOAc (3×5 mL)
4. 4
   WaschenThe combined extracts were washed with water (5×20 mL), saturated brine (2×20 mL)
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeEvaporation of the solvent

Vorschrift

To 6-chloro-nicotinic acid (415 mg, 2.59 mmol), was added 3-hydroxytetrahydrofuran (468 mg, 5.16 mmol), potassium hydroxide (579 mg, 10.3 mmol) and DMSO (5 mL). The mixture was heated at 120 C for 24 h. Further potassium hydroxide (579 mg) and 3-hydroxytetrahydrofuran (468 mg) was added and the mixture heated at 120 C for 24 h. The reaction was allowed to cool to room temperature, acidified to pH=1-2 with a 2M aq. solution of HCl (13 mL) and extracted into EtOAc (3×5 mL). The combined extracts were washed with water (5×20 mL), saturated brine (2×20 mL) and dried over anhydrous sodium sulfate. Evaporation of the solvent afforded the title compound as an orange solid which was dried under high vacuum to remove traces of solvent (209 mg, 39%). Method B HPLC-MS: MH+ requires m/z=210. Found: m/z=210, Rt=1.32 min (100%).

Quelle