تفاعل #157126

معادلة التفاعل

NaH

2-methyl-1-propanol

2,6-dichloropyrazine

→

2-chloro-6-isobutoxypyrazine

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction was warmed to rt
2. 2
   أخرىThe crude mixture was quenched with saturated aqueous NH4Cl
3. 3
   استخلاصextracted with EtOAc
4. 4
   غسيلThe combined organic phases were washed once each with H2O and brine
5. 5
   تجفيفdried over anhydrous Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuo
8. 8
   workup.DISSOLUTIONThe crude residue was dissolved in CH2Cl2
9. 9
   أخرىpurified by flash chromatography (9:1 hexanes/EtOAc eluent)

الإجراء التجريبي

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+).

المصدر