(E)-1-Bromo-3,3-diethoxy-1-propene (diethyl acetal of 3-bromoacrolein). A versatile synthon for the synthesis of furans, butenolides, and (Z)-allyl alcohols
A convenient preparation of the title compound allowed a study in which the .alpha.-lithio-.alpha.-bromovinyl acetal 2 could be evaluated as a precursor to furans, butenoliddes, and (Z)-allyl alcohols. Reaction of the lithio derivative with aldehydes, ketones, and alkyl halides took place in a conve...
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Published in | Journal of organic chemistry Vol. 50; no. 24; pp. 4872 - 4877 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.11.1985
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | A convenient preparation of the title compound allowed a study in which the .alpha.-lithio-.alpha.-bromovinyl acetal 2 could be evaluated as a precursor to furans, butenoliddes, and (Z)-allyl alcohols. Reaction of the lithio derivative with aldehydes, ketones, and alkyl halides took place in a convenient manner. The bromine was either transformed at a later stage to an alkyl group or reduced to hydrogen with tin hydrides. The carbonyl adducts of 2 could be transformed, on mild hydrolysis, to butenolides or 2,3-disubstituted furans. An interesting solvent system (1:1:1 THF-Et2O-pentane) allowed vinyl proton abstraction and halogen-metal exchange to take place in one pot. |
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Bibliography: | ark:/67375/TPS-CQ6F6QHR-P istex:5FFE2A0D1A1D73924573D4FCA31D6CB528EDA3AF |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo00224a044 |