Réaction #43717

Équation de réaction

methanesulfonyl chloride

2-chloro-3-cyanobenzaldehyde

sodium hydride

methyl mercaptoacetate

→

Methyl6-cyano-1-benzothiophene-2-carboxylate

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   AutreThe resulting reaction product
2. 2
   Autreis initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1)
3. 3
   workup.DISSOLUTIONdissolved in 30 ml of pyridine
4. 4
   TempératureAfter cooling
5. 5
   Lavagethe mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution
6. 6
   Séchagedried over sodium sulfate
7. 7
   Concentrationconcentrated
8. 8
   Autredried under high vacuum

Mode opératoire

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.

Source