Hydrochloric Acid → HCID 90423706, compound

Participants

Reaction Conditions

Reaction Steps

Tris(dibenzylideneacetone)dipalladium(0) (2.30 g) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (2.21 g) were added to a mixture of 3-ethoxy-5-iodo-4-(methoxymethoxy)benzaldehyde (12.1 g), cyclopropylboronic acid (9.25 g), a 2 M aqueous sodium carbonate solution (53.9 mL), and toluene (60 mL), and the resultant mixture was stirred at 100° C. for 2 hours in an argon atmosphere. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain a purified product. 6 M hydrochloric acid (50 mL) was added to a methanol (100 mL) solution of the obtained purified product, and the mixture was stirred at 70° C. for 3 hours, and then, the solvent was distilled off under reduced pressure, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (6.60 g).

Provenance & Evidence