Ethyl Acetate → [5-(4-Chlorophenyl)-2-furyl]methanol

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The product from Example 11A (1.012 g, 5.72 mmol) in 10 mL of DMF was treated sequentially with PdCl2 (PPh3)2 (401 mg, 0.57 mmol), 4-chlorophenylboronic acid (1.78 g, 11.4 mmol), and Cs2CO3 (3.71 g, 11.4 mmol). The reaction was heated at 80° C. under N2 for 12 hours. The reaction mixture was taken up in ethyl acetate and washed with water (3×) and brine (3×), dried (Na2SO4), filtered, and evaporated to a brown oil that was purified by flash chromatography (50% ethyl acetate/hexanes) to provide 345 mg (35%) the title compound as an oil.

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