Cesium carbonate → (5-Phenylfuran-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

The 5-bromo-2-hydroxymethylfuran prepared in Example 327A (1.012 g, 5.72 mmol) was dissolved in 10 mL of DMF and PdCl2 (PPh3)2 (401 mg, 0.57 mmol) was added followed by phenylboronic acid (1.39 g, 11.4 mmol) and Cs2CO3 (3.71 g, 11.4 mmol) and 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 over Na2SO4, filtered and evaporated to a brown oil that was purified by flash chromatography (50% ethyl acetate-hexanes) to give the desired compound (345 mg, 35%) as an oil.

Provenance & Evidence