HCID 59627705, compound → HCID 59627702, compound

Participants

Reaction Conditions

Reaction Steps

Iron powder (193 mg, 3.46 mmol) was added to a stirred solution of ethyl 2-chloro-2-(5-chloro-4-methoxy-2-methylphenyl)acetate (Intermediate 3-5; 480 mg, 1.73 mmol) in AcOH (2 mL) under nitrogen, and the resulting mixture was stirred at 60° C. for 17 hours. The reaction mixture was allowed to cool to ambient temperature, diluted with EtOAc (50 mL), filtered through celite and washed with saturated brine (3×25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)acetate (190 mg, 45.2%) as a colourless gum.

Provenance & Evidence