Réaction #595153

Équation de réaction

1-chloro-2-ethoxyethane

3,5-dimethylbenzenethiol

potassium carbonate

potassium iodide

→

title compound

Rendement 76.2%

2-[(3,5-dimethylphenyl)thio]ethyl ethyl ether

Rendement 76.2%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred at 80° C. for 5 hr
2. 2
   ConcentrationThe reaction mixture was concentrated under reduced pressure, and water
3. 3
   workup.ADDITIONwas added to the residue
4. 4
   ExtractionThe mixture was extracted with diethyl ether
5. 5
   SéchageThe extract was dried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=10/1)

Mode opératoire

To a solution of 1-chloro-2-ethoxyethane (5.90 mL, 54.3 mmol) and 3,5-dimethylbenzenethiol (5.00 g, 36.2 mmol) in N,N-dimethylformamide (140 mL) were added potassium carbonate (5.50 g, 39.8 mmol) and potassium iodide (0.90 g, 5.43 mmol) under stirring at room temperature, and the mixture was stirred at 80° C. for 5 hr. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=10/1) to give the title compound (5.80 g, yield 76%) as a colorless oil.

Source