Synthesis of Substituted 2,3-Dihydrobenzofuran in a Process Involving a Facile Acyl Migration.
2002
Abstract Reduction of 2,6-diacetoxy-2′-bromoacetophenone ( 10 ) with NaBH 4 led to 3,4-diacetoxydihydrobenzofuran ( 12 ) in a process involving acyl migration followed by cyclization. Subsequent hydrogenolysis gave 4-acetoxydihydrobenzofuran which, upon saponification, afforded 4-hydroxydihydrobenzofuran ( 8 ) in good yield. This approach is shown to be a general method for preparation of substituted dihydrobenzofurans.
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