Synthesis of substituted 2, 3-dihydrobenzofuran in a process involving a facile acyl migration

…, J Thornton, K Katipally, R Polniaszek, J Thottathil…

Index: Li, Wen-Sen; Guo, Zhenrong; Thornton, John; Katipally, Kishta; Polniaszek, Richard; Thottathil, John; Vu, Truc; Wong, Michael Tetrahedron Letters, 2002 , vol. 43, # 11 p. 1923 - 1925

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Citation Number: 14

Abstract

Reduction of 2, 6-diacetoxy-2′-bromoacetophenone (10) with NaBH4 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.