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Methyl (<i>E</i>)-4-Chloro-3-methoxy-2-butenoate: An Extremely Versatile Four Carbon Building Block
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1992
Year
Chemical EngineeringEngineeringCarbon Building BlockUnprotected Parent CompoundOrganic ChemistryOrganometallic CatalysisCatalysisChemistryHalogenationSynthetic ChemistryThionyl ChlorideIndustrial ScaleNatural Product Synthesis
Methyl (E)-4-chloro-3-methoxy-2-butenoate (3a) is inexpensively prepared from methyl 4-chloroacetoacetate using thionyl chloride and methanol on an industrial scale. Many nucleophilic substitution reactions of chloride, which are impossible with the unprotected parent compound proceed readily with 3a.