(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

• Published in: Journal of organic chemistry Vol. 50; no. 24; pp. 4872 - 4877
• Main Authors: Meyers, A. I, Spohn, Ronald F
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.11.1985; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Solvent effect; Five membered ring; Aliphatic compound; Benzaldehyde; Lactone; Alkanal; Aldehyde; Enaldehyde; Oxygen heterocycle; Ketone; Alkylation; Allylic compound; Primary alcohol; Hydrolysis; Acetal; Lithium Organic compounds; Lithiation
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo00224a044

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.