✦ LIBER ✦

1,4-Diazobicyclo[2.2.2]octane-catalyzed coupling of aldehydes and activated double bonds. Part 3. A short ans practical synthesis of mikanecic acid (4-vinyl-1-cyclohexene-1,4-dicarboxylic acid)

✍ Scribed by H. M. R. Hoffmann; Jürgen Rabe

Book ID: 102253182
Publisher: John Wiley and Sons
Year: 1984
Tongue: German
Weight: 185 KB
Volume: 67
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19840670209

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✦ Synopsis

Abstract

The title dicarboxylic acid 1d has been prepared in 24% overall yield via, 1,4‐diazabicyclo[2.2.2]octane (DABCO)‐catalyzed coupling of ethanal and tert‐butyl propenoate (3) to 4, S~N~2′‐reaction to tert‐butyl (Z)‐2‐romomethyl‐2‐butenoate (5a), dehydrobrominatin to tert‐butyl 2‐methylidene‐3‐butenoate (2c), dimerizatoin to di‐tert‐butyl 4‐vinyl‐1‐cyclohexene‐1,4‐dicarboxylate (1c) and acidic ester cleavage. Acidic cleavage of easily obtainable 5a affords (Z)‐2‐bromomethyl‐2‐butenoic acid (5a) in 68% yield with respect to ethanal.

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