Ethoxalyl chloride → HCID 67191294, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask is placed methylene chloride (100 mL) and aluminum trichloride (1.39 equiv) and it is cooled to 0° C. in an ice bath. To this solution is then added dropwise chloro-oxo-acetic acid ethyl ester (1.09 equiv.) keeping the temperature of the solution below 5° C. and it is then stirred for 30 min at 0° C. After this time a solution of 1-chloro-2-cyclopentylsulfanyl-benzene (50.0 mmol) in methylene chloride (5 mL) is added dropwise while keeping the temperature of the solution below 5° C. The ice bath is then removed and the reaction is allowed to warm up to 25° C. and is stirred for 3 h. The reaction is then cooled back down to 0° C. in an ice bath and ice water (20 mL) is then added dropwise keeping the temperature of the solution below 20° C. It is then stirred for 15 min and then transferred to a separatory funnel and separated. The organic phase is then washed with water (2×25 mL), saturated aqueous sodium bicarbonate solution (2×25 mL) and water (25 mL) and then dried over magnesium sulfate, filtered and concentrated in vacuo to afford (3-chloro-4-cyclopentylsulfanyl-phenyl)-oxo-acetic acid ethyl ester.

Provenance & Evidence