تفاعل #43717

معادلة التفاعل

methanesulfonyl chloride

2-chloro-3-cyanobenzaldehyde

sodium hydride

methyl mercaptoacetate

→

Methyl6-cyano-1-benzothiophene-2-carboxylate

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction product
2. 2
   أخرىis initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1)
3. 3
   workup.DISSOLUTIONdissolved in 30 ml of pyridine
4. 4
   درجة الحرارةAfter cooling
5. 5
   غسيلthe mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution
6. 6
   تجفيفdried over sodium sulfate
7. 7
   تركيزconcentrated
8. 8
   أخرىdried under high vacuum

الإجراء التجريبي

2.5 g (15.1 mmol) of 2-chloro-3-cyanobenzaldehyde are reacted according to the general procedure with 0.90 g (22.7 mmol) of sodium hydride (60% pure) and 1.76 g (16.6 mmol) of methyl mercaptoacetate. The resulting reaction product is initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1) and then dissolved in 30 ml of pyridine, and 650 μl (8.4 mmol) of methanesulfonyl chloride are added. The mixture is stirred at 80° C. for 2 h. After cooling, ethyl acetate is added and the mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution, dried over sodium sulfate, concentrated and dried under high vacuum. This gives 1.63 g (49.9% of theory) of the title compound.

المصدر