Application
2-Phenyran is a substituted furan. Furans are widely used oxygen-containing five-membered heterocyclic compounds, representing an important class of molecular structures. This structure is widely found in natural products and drug molecules, often serving as a building block in the synthesis of many complex heterocyclic compounds. There are many homologues of furan, and these products have wide applications, primarily as raw materials for novel pharmaceuticals, pesticides, fragrances, and chemical auxiliaries. In recent years, in particular, many novel drugs containing furan rings have been developed abroad, showing promising development prospects.
Synthesis
To a dry reaction flask was added dichloroditritophenylphosphine palladium (14 mg, 0.02 mmol), cuprous iodide (1.9 mg, 0.01 mmol), triethylamine (2 ml), iodobenzene (204 mg, 1 mmol), and 3-butyn-1-ol (84 mg, 1.2 mmol), and the reaction was carried out for 3 h at 50 C. The reaction was quenched with a 1:1 mixture of ethyl acetate and water. The reaction was quenched with a 1:1 solution of ethyl acetate and water, stirred for 0.5 h. The aqueous layer was extracted with ether, the organic layers were combined, the organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, spun-dried, and subjected to rapid column chromatography (mobile phase: petroleum ether/ethyl acetate = 10:1) to afford 134 mg of the intermediate 4-phenyl-3-butyn-1-ol in 92% yield. To 4-phenyl-3-butyn-1-ol 73 mg (0.5 mmol) was added 5 ml of dichloroethane and Dess-Martin Periodinane (318 mg, 0.75 mmol), protected by nitrogen at room temperature, stirred for 1 h. The reaction was quenched with saturated sodium bicarbonate, extracted with ether for 3 times, washed with saturated brine to wash the organic phase, dried with anhydrous sodium sulfate, and rapid Column chromatography (mobile phase: petroleum ether), spinning to remove the solvent, the colorless liquid product 2-phenylfuran 52mg, yield 72%.
