Reaktion #68908

Reaktionsgleichung

(S)-glycidyl 3-nitrobenzene sulfonate

6-Methyl-pyridin-3-ol

NaH

→

title compound

(S)-2-Methyl-5-oxiranylmethoxy-pyridine

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwas then stirred at room temperature for 14 hours
2. 2
   SonstigeThe reaction was quenched with NaHCO3 (saturated)
3. 3
   Extraktionextracted three times with ethyl acetate
4. 4
   TrocknenThe organic layer was dried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   Sonstigeto yield crude product which
8. 8
   Sonstigewas purified by silica gel chromatography (60% Ethyl acetate/heptane)

Vorschrift

6-Methyl-pyridin-3-ol (0.218 g, 2.0 mmol) was placed in a flask with DMF (10 mL) and NaH (60% dispersion in oil, 77 mg, 2.0 mmol) and stirred for 30 min. at room temperature. (S)-glycidyl 3-nitrobenzene sulfonate (0.52 g, 2.0 mmol) was then added to the reaction mixture, which was then stirred at room temperature for 14 hours. The reaction was quenched with NaHCO3 (saturated) and then extracted three times with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and the solvent was evaporated under reduced pressure to yield crude product which was purified by silica gel chromatography (60% Ethyl acetate/heptane) to yield the title compound as a residue.

Quelle