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(E)-3-(Trimethylsilyl)-2-propen-1-ol. An improved preparation

โœ Scribed by Denmark, S. E.; Jones, T. K.

Book ID
127287876
Publisher
American Chemical Society
Year
1982
Tongue
English
Weight
423 KB
Volume
47
Category
Article
ISSN
0022-3263

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The tetrahydropyranyl ether of (E)-3-bromo-3-trimethylsilyl-2-propen-l-01 can serve as a single synthon for both the (E)-B-formylvinyl anion and cation depending upon the manner in which the bromine group is stereospecifically replaced by an alkyl group. mmol, 80% yield) of colorless product. GLC a

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## Abstract Methyl cinnamate โ€3โ€^14^C is reduced smoothly in excellent yield to cinnamyl alcohol โ€3โ€^14^C by aluminum hydride. without attack of the double bond. After purification by column chromatography cinnamyl alcohol โ€3โ€^14^C is obtained with a radioactive overall yield of 65% based on cinnam