Synthesis of 3-methyl-5, 6-dihydro-3H-benzofuro [3, 2-e] isoquinolin-7 (7aH)-ones

DD Weller, EP Stirchak, DL Weller

Index: Weller, Dwight D.; Stirchak, Eugene P.; Weller, Doreen L. Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4597 - 4605

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Citation Number: 29

Abstract

First, since the 3-methoxy analogue of 6 is not commercially available, extra steps were necessary to prepare the acetophenone 7b. o-Vanillin was treated with benzyl iodide and potassium carbonate to give the corresponding benzyl ether. Addition of methyllithium, followed by pyridinium chlorochromate oxidation of the resulting alcohol, gave acetophenone derivative 7b in 80% overall yield. As in the model series, Grignard ...