تفاعل #1147068

معادلة التفاعل

2-chloro-4-methylthiazole

n-butyllithium

tetrahydrofuran

2-cyano-4-methylpyridine

tetrahydrofuran

ammonium chloride

→

2-chloro-4-methyl-5-(4-methylpyridin-2-ylcarbonyl)thiazole

المذيبات

n-hexane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred for 15 minutes
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with brine
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   أخرىevaporated
6. 6
   أخرىThe residue was purified by column chromatography (silica gel 240 g, n-hexane:ethyl acetate=10:1)

الإجراء التجريبي

To a stirred solution of 2-chloro-4-methylthiazole (6.35 g) in tetrahydrofuran (50 ml) was added a solution of n-butyllithium in n-hexane (1.66M, 34.35 ml) dropwise at −70° C. under a nitrogen atmosphere, and the mixture was stirred for 20 minutes at −70° C. To the resultant mixture was added a solution of 2-cyano-4-methylpyridine (3.74 g) in tetrahydrofuran (30 ml) dropwise at −70° C., and the mixture was stirred for 15 minutes. The mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography (silica gel 240 g, n-hexane:ethyl acetate=10:1) to give 2-chloro-4-methyl-5-(4-methylpyridin-2-ylcarbonyl)thiazole (1.64 g).

المصدر