Hydrochloric Acid → Methyl 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoate

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Reaction Steps

A mixture of tris(dibenzylideneacetone)dipalladium (0) (163 mg), 1,1′-bis(diphenylphosphino)ferrocene (394 mg) and N,N-dimethylformamide (10 mL) was stirred under an argon atmosphere for 10 minutes. 3-(4-Benzyloxy-2-iodo-5-methoxy-phenyl)-5-methyl-[1,2,4]oxadiazole (reference example 4-1) (1.5 g), methanol (15 mL) and triethylamine (1.5 mL) were added to the mixture. After displacement to a carbon monoxide atmosphere, the mixture was stirred at 90° C. for 16 hours. After cooling to room temperature, ethyl acetate and 2 mol/L hydrochloric acid were added to the mixture. The separated organic layer was washed with water, a 2 mol/L aqueous solution of sodium hydroxide, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 15%-30% ethyl acetate/hexane, gradient elution) to give the title compound (1.1 g).

Provenance & Evidence