Water → HCID 70818481, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, ethyl chlorooxoacetate (898 μL, 8.04 mmol) and aluminum chloride (III) (2.14 g, 16.07 mmol) were added successively at −10° C. to a solution of 3-bromo-2-chloro-5-methylthiophene (44a) (1.7 g, 8.04 mmol) in dichloromethane (84 mL). After 1 hour at 0° C., the mixture was stirred at room temperature for 8 hours. The reaction mixture was slowly hydrolyzed at 0° C. with water. The organic layer was separated, washed with hydrochloric acid 1 N, brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to give the desired keto-ester (44b) as an orange solid (1.44 g, 4.6 mmol, 56%).

Provenance & Evidence