Reacción #157126

Ecuación de reacción

NaH

2-methyl-1-propanol

2,6-dichloropyrazine

→

2-chloro-6-isobutoxypyrazine

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction was warmed to rt
2. 2
   OtroThe crude mixture was quenched with saturated aqueous NH4Cl
3. 3
   Extracciónextracted with EtOAc
4. 4
   LavadoThe combined organic phases were washed once each with H2O and brine
5. 5
   Secadodried over anhydrous Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   workup.DISSOLUTIONThe crude residue was dissolved in CH2Cl2
9. 9
   Otropurified by flash chromatography (9:1 hexanes/EtOAc eluent)

Procedimiento

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+).

Fuente