New synthesis of 2-aryl-3-substituted benzo[b]furans from benzyl 2-halophenyl ethers |
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Authors: | Sanz Roberto Miguel Delia Martínez Alberto Pérez Antonio |
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Institution: | Departamento de Química, Area de Química Organica, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Ba?uelos s/n, 09001-Burgos, Spain. rsd@ubu.es |
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Abstract: | Treatment of benzyl 2-halophenyl ethers with 3 equiv of t-BuLi results in Li-halogen exchange and lithiation at benzylic methylene simultaneously. These dianions do not undergo Wittig rearrangement and can be trapped with electrophiles. Their reactions with carboxylic esters afford the corresponding 2-aryl-3-hydroxy-2,3-dihydrobenzob]furans as a mixture of diastereoisomers. Subsequent acid-catalyzed or mediated dehydration gives moderate to good overall yield of a variety of 2-aryl-3-substituted benzob]furans. |
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