2-Lithio-3-methoxy-1, 3-dimethylcyclopentene: A Synthetic Equivalent of 2-Lithio-1, 3-dimethylcyclopentadiene and Useful Synthon for 6-Alkyl-1, 4-dimethylfulvenes …

YC Won, UG Joung, ES Cho, BY Lee, H Lee…

Index: Won, Young Chul; Joung, Ui Gab; Cho, Eun Sook; Lee, Bun Yeoul; Lee, Hyosun; Park, Young-Whan; Song, Kwang Ho Synthesis, 2004 , # 7 p. 1052 - 1056

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Citation Number: 6

Abstract

Abstract 2-Bromo-3-methoxy-1, 3-dimethylcyclopentene (3) is synthesized in 85% yield in 80 g scale by 1, 2-addition of MeLi to 2-bromo-3-methyl-2-cyclopenten-1-one and subsequent in situ treatment of MeI. Addition of n-BuLi to the bromo-compound 3 in Et 2 O affords 2-lithio- 3-methoxy-1, 3-dimethylcyclopentene (1). Successive addition of RCHO [R= CH 3,(CH 2) 2 CH 3, CH (CH 3) 2, C (CH 3) 3, H] and MeI to the lithium compound and aqueous acidic ...