2-methoxyethylsulfanylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl chloroglyoxylate (8.76 mL) was added dropwise to a suspension of aluminum chloride (13.2 g, crushed) in methylene chloride (127 mL) under stirring and cooling with ice, and (2-methoxyethyl)phenylsulfide (12.0 g) was added dropwise thereto. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water (200 mL), and the mixture was stirred for 10 minutes. The organic layer was separated, washed with a saturated aqueous sodium hydrogen carbonate solution (40 mL×3), and washed with saturated brine (60 mL). The washed organic layer was dried over anhydrous sodium sulfate, filtrated, and evaporated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:1) to give 2-[4-(2-methoxyethylthio)phenyl]-2-oxoacetic acid ethyl ester (1.98 g). was added dropwise The mixture was stirred at room temperature for 2 hours the mixture was stirred for 10 minutes The organic layer was separated washed with a saturated aqueous sodium hydrogen carbonate solution (40 mL×3) washed with saturated brine (60 mL) The washed organic layer was dried over anhydrous sodium sulfate filtrated evaporated under reduced pressure The obtained residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:1)