Ethanol → 5-Ethoxypyrimidine
Reaktionsgleichung
[Na].Br[C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1.[CH2:9]([OH:11])[CH3:10]>>[CH2:9]([O:11][C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1)[CH3:10]Komponenten
4
Versuchsvorschrift
Sodium (2.89 g. 125.8 mmol) was dissolved in ethanol (110 mL) and 5-bromopyrimidine (10.0 g, 62.9 mmol) added. The reaction was heated at 120° in an autoclave for 17 h and then allowed to stand at 23° for 60 h. The ethanol was removed under reduced pressure and water (5 mL) added to the concentrate. The aqueous phase was extracted with CH2Cl2 (4×100 mL). The combined organic extracts were washed with saturated NaCI solution, dried with anhydrous K2CO3, filtered, and concentrated under reduced pressure. Silica gel chromatography (Hexane/EtOAc; 70:30) of the concentrate yielded 5-ethoxypyrimidine (2.00 g, 25.6%).