Acrolein → t-butyl {2-chloro-5-[(1E)-3-oxo-1-propenyl]phenoxy}acetate

Participants

Reaction Conditions

Reaction Steps

t-Butyl (2-chloro-5-iodophenoxy)acetate (851 mg, 2.00 mmol) was dissolved in dimethylformamide under an atmosphere of nitrogen, and thereto were acrolein (0.400 ml, 6.00 mmol), sodium carbonate (0.510 g, 6.00 mmol), benzyltriethylammonium chloride (683 mg, 3.00 mmol) and palladium acetate (14.0 mg, 60.0 μmol). The mixture was stirred for 3 hours at 60° C. The reaction mixture was cooled and thereto was added sodium thiosulfate. The mixture was extracted with ethyl acetate and the organic layer was washed with sodium thiosulfate, 10% aqueous citric acid solution, water, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in the order, and dried over magnesium sulfate. The solvent was removed to give the subject compound as yellow crystals (631 mg, quantitatively).

Provenance & Evidence