Synthesis of α, β-Ethylenic Esters in a Heterogenous Solid-Liquid Medium. II - A Transesterification Reaction Linked to a Wittig-Horner Reaction in a Protic Medium

References

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• The reaction products were generally separated and purified by chromatography on a silica column with an ether/hexane 4/1 (V/V) mix used as eluant. The weighed yields are presented in table except (9)
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• The reaction carried out at 25° C with Rb2CO3 as catalyst was done with a selective formation of furfurylidene-2 furfuryl acetate in 3 hours giving the same yield after distillation (Eb = 105° C/1 torr)
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• The chemical shifts of the Hα and Hβ protons (δ = 6.1 Hz ± 0.2ppm, 7.3 Hz ± 0.2ppm) and the observed coupling constant (JHαHβ = 16Hz) are characteristic of the selectively achieved E-alkene in this reaction
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• Ethyl phosphonate was used in all the tests reported in this table except in this reaction, carried out in atmospheric pressure, where methyl phosphonate was employed
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• Reaction products were separated and purified by chromatography on a silica column with a dichloromethane/hexane 4/1 (V/V) mix as eluant. Weighed yields are presented in the table
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• Reaction under reduced pressure (20 imiHg)
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