反应详情

To a round bottom flask containing 1-benzyl-4-bromo-benzene (700 mg, 2.83 mmol) and 5-formyl-2-furan-boronic acid (595 mg, 4.25 mmol) in dimethoxyethane (30 mL) and ethanol (7.5 mL) was added an aqueous solution of sodium carbonate (900 mg, 8.49 mmol) in water (10 mL) The reaction mixture was stirred at room temperature for 5 minutes, followed by the addition of tetrakis(triphenylphosphine)palladium (162 mg, 0.14 mmol). The reaction was heated at 70° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and water (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated under vacuum. The crude product was purified by silica gel chromatography eluting with 6% ethyl acetate in hexanes to afford 5-(4-benzyl-phenyl)-furan-2-carbaldehyde (320 mg g, 43%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 3.99 (2H, s), 7.20-7.39 (8H, m), 7.63 (1H, d, J=3.6 Hz), 7.78-7.81 (2H, m), 9.59 (1H, s); APCI-MS: 262.02.

1. temperatureThe reaction was heated at 70° C. for 1 h
2. temperatureThe reaction mixture was cooled to room temperature
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
5. washThe combined organic extracts were washed with brine
6. dry with materialdried (sodium sulfate)
7. concentrationconcentrated under vacuum
8. customThe crude product was purified by silica gel chromatography
9. washeluting with 6% ethyl acetate in hexanes