Hydrochloric Acid → HCID 14275054, compound

Participants

Reaction Steps

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 4.4 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (1.74 g, 6.61 mmol) in THF (30 mL) at −78° C. and the mixture solution was stirred at the same temperature for one hour. To this solution, a solution of 3,4-dimethoxybenzaldehyde (1.00 g, 6.02 mmol) in THF (8 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for 1.5 hours, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure to obtain a crude product (2.38 g). The obtained crude product was dissolved in methanol (20 mL) and a 20% palladium hydroxide catalyst (196 mg) was added and furthermore 2N—HCl (30 μL) was added thereto. The mixture solution was stirred under a hydrogen atmosphere for 23 hours, and then the catalyst was filtered off. The solvent was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (653 mg, 44%).

Provenance & Evidence