Ethyl bromoacetate → Ethyl 2-methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetate

Participants

Reaction Steps

To an ice-cold suspension of the above-mentioned 1-(4-hydroxy-3-methylphenyl)-3-(3-methylbenzothiophen-2-yl)propan-1-one (200 mg, 0.644 mmol) and potassium carbonate (178 mg, 1.29 mmol) in acetone (6.4 mL) was added slowly ethyl bromoacetate (0.14 mL, 1.3 mmol). The mixture was heated under reflux for 3 hours, to which was added saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1), to give the titled compound as a colorless oil (223 mg, yield 87%).

Provenance & Evidence