Reaktion #157126

Reaktionsgleichung

NaH

2-methyl-1-propanol

2,6-dichloropyrazine

→

2-chloro-6-isobutoxypyrazine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction was warmed to rt
2. 2
   SonstigeThe crude mixture was quenched with saturated aqueous NH4Cl
3. 3
   Extraktionextracted with EtOAc
4. 4
   WaschenThe combined organic phases were washed once each with H2O and brine
5. 5
   Trocknendried over anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   workup.DISSOLUTIONThe crude residue was dissolved in CH2Cl2
9. 9
   Sonstigepurified by flash chromatography (9:1 hexanes/EtOAc eluent)

Vorschrift

A flame-dried round bottom flask was charged with a suspension of 95% NaH (1.1 eq) in anhydrous THF (0.3 M). The stirring mixture was cooled to 0° C. in an ice-water bath and 2-methyl-1-propanol (1 eq) was added drop wise via syringe. After 30 min 2,6-dichloropyrazine (1 eq) was added, the reaction was warmed to rt and stirred for 3 h. The crude mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were washed once each with H2O and brine, then dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was dissolved in CH2Cl2, loaded onto a SiO2 column, and purified by flash chromatography (9:1 hexanes/EtOAc eluent) to give 2-chloro-6-isobutoxypyrazine. LC/MS (m/z): 187.1 (MH+).

Quelle