Reaktion #1835745

Reaktionsgleichung

mesyl chloride

4-(5-Bromo-3-methylpyridin-2-yl)-tetrahydro-2H-pyran-4-ol

triethylamine

trimethylamine monohydrochloride

→

titled compound

Ausbeute 86.8%

5-Bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-methylpyridine

Ausbeute 86.8%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder ice-cooling
2. 2
   workup.ADDITIONwas added
3. 3
   Extraktionextracted with chloroform
4. 4
   Trocknenthe organic layer was dried over anhydrous sodium sulfate
5. 5
   Sonstigethe solvent was evaporated in vacuo
6. 6
   SonstigeThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Vorschrift

4-(5-Bromo-3-methylpyridin-2-yl)-tetrahydro-2H-pyran-4-ol (2.95 g), triethylamine (3 ml) and trimethylamine monohydrochloride (103 mg) were suspended in toluene (50 ml), mesyl chloride (1.26 ml) was added thereto under ice-cooling, then warmed to room temperature, and stirred for 72 hours. After completion of the reaction, water was added thereto, extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (2.39 g) as a white solid. MS (ESI) m/z: 254, 256 (M+H)+.

Quelle