Water → 2'-methyl-4'-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

2-(4-Bromo-3-methylphenoxy)tetrahydro-2H-pyran (7.11 g, 25.2 mmol, including 3,4-dihydro-2H-pyran) and (3-formylphenyl)boronic acid (4.50 g, 30.0 mmol) were dissolved in a mixture of 1 M aqueous sodium carbonate solution (60 mL), ethanol (30 mL) and toluene (60 mL), and after argon substitution, tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.50 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 80° C. for 15 hrs. The reaction mixture was cooled, water and ethyl acetate were added, and insoluble material was filtered off through celite. The organic layer of the filtrate was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane) to give the title compound (6.16 g, yield 82%, 2 steps) as a pale-yellow oil.

Provenance & Evidence