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A simple route to α,β-unsaturated aldehydes from propargylic alcohols

✍ Scribed by E.J. Corey; Shiro Terashima

Publisher
Elsevier Science
Year
1972
Tongue
French
Weight
112 KB
Volume
13
Category
Article
ISSN
0040-4039

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✦ Synopsis

In connection with the study of new approaches to the synthesis of prostaglandins, a method of preparation of tram+2-octena1 (IV) was sought whfch would be simpler and more expeditious than existing methods (1). We report here a new process which has been found to be highly satisfactory and convenient for either small or large scale synthesis.

Commercially available 2-octyn-l-01 (I) (2) was converted into the tetrahydropyranyl derivative (II) (3) in quantitative yield by treatment with 1.1 equiv. of 2,3-dlhydropyran and 0.005 equiv. of R-toluenesulfonic acid in methylene chloride (12 ml. /g. of I) at 25' for 30 min. Metalation of II to form a propargylic ltthlum

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