Hydrochloric Acid → HCID 80277746, compound

Participants

Reaction Steps

Methyl methylsulfinylmethyl sulfide (5.53 g) and potassium hydroxide (2 g) were added to a solution of 5-chloro-2-thiophenecarboxyaldehyde (6.21 g) in methanol (70 mL), and the reaction solution was stirred with heating under reflux for 21 hours. After leaving to cool to room temperature, the solvent was evaporated under reduced pressure. Methylene chloride was added to the residue, the insoluble matter was removed by filtration, and the solvent was evaporated under reduced pressure. Then, the residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 5.61 g of a (E)/(Z) mixture of 2-chloro-5-(2-methanesulfinyl-2-methylsulfanylvinyl)thiophene. A saturated solution of hydrogen chloride in ethanol (10 mL) was added to a solution of the resulting (E)/(Z) mixture of 2-chloro-5-(2-methanesulfinyl-2-methylsulfanylvinyl)thiophene (5.61 g) in ethanol (80 mL), and the reaction solution was stirred with heating under reflux for 23 hours. After leaving to cool to room temperature, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 3.31 g of the title compound. The property values of the compound are as follows.

Provenance & Evidence