Reaktion #648186

Reaktionsgleichung

6-fluoro-4-iodo-pyridin-3-ol

sodium hydride

2-(2-bromo-ethoxy)-tetrahydro-pyran

→

title compound

Ausbeute 75.6%

2-Fluoro-4-iodo-5-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-pyridine

Ausbeute 75.6%

Lösungsmittel

ethyl acetate

water

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGStir the solution at room temperature overnight
2. 2
   WaschenWash the organic layer with saturated aqueous sodium chloride and water
3. 3
   TrocknenDry the mixture over sodium sulfate
4. 4
   EinengenConcentrate the solution in vacuo
5. 5
   Sonstigeto give yellow oil
6. 6
   SonstigePurify the oil by column chromatography (10% ethyl acetate in hexane)

Vorschrift

Add 6-fluoro-4-iodo-pyridin-3-ol (0.5 g, 2.09 mmol) to a suspension of sodium hydride (60% dispersion in mineral oil, 0.1 g, 2.51 mmol) in dimethylformamide (6 mL). Stir the mixture for 1 hour. Add 2-(2-bromo-ethoxy)-tetrahydro-pyran (0.51 g, 2.34 mmol). Stir the solution at room temperature overnight. Dilute the mixture with ethyl acetate and water. Wash the organic layer with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to give yellow oil. Purify the oil by column chromatography (10% ethyl acetate in hexane) to afford the title compound (0.58 g, 75.5%) as a light yellow oil. MS (EI) m/z 368 [M+1]+.

Quelle