The Journal of Organic Chemistry

Improved synthesis of 3-methylcholanthrene

PW Tang, CA Maggiulli

Index: Tang, Ping Wah; Maggiulli, Cataldo A. Journal of Organic Chemistry, 1981 , vol. 46, # 17 p. 3429 - 3432

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Citation Number: 3

Abstract

An improved synthesis of 7-methylindan-4-yl 1-naphthyl ketone (3), an important precursor, of 3-methylcholanthrene (I), has been developed. The key intermediates for 3, 4-cyano-7- methylindan (2a) and 4-(eth-oxycarbonyl)-7-methylindan (2b), were conveniently prepared in high yields by reaction of 1-(1-pyrro1idino)-cyclopentene (6) with sorbonitrile (5a) or ethyl sorbate (5b), followed by aromatization with sulfur. 1-Naphthylmagnesium bromide (4b) in ...