Methyl 2 3-butadienoate

Uses

Methyl 2,3-Butadienoate is used as an reactive electrophilic reagents for nucleophilic addition, Michael addition, [2 + 2], [2 + 3], and [2 + 4] cycloadditions, and hetero-Cope rearrangements.

Preparation

Methyl 2,3-Butadienoate is most conveniently obtained via a Wittig reaction of [E(R)CHPPh3]+X- or E(R)C=PPh3 and RR′CHCOCl (R, R′ = H, alkyl) in the presence of Triethylamine in CH2Cl2.^[1]Alternatively, the Wittig reaction can be performed with the corresponding ketenes.^[2]

Synthesis Reference(s)

Tetrahedron Letters, 13, p. 4249, 1972 DOI: 10.1016/S0040-4039(01)94287-X

storage

Methyl 2,3-Butadienoate can undergo polymerization and so should be stored in the presence of hydroquinone. For best results, it should be freshly distilled. Use in a fume hood.

Purification Methods

Purification of Methyl 2,3-Butadienoate: rapid distillation under reduced pressure in a short-path distillation apparatus or column chromatography on Alox N with hexane/Et2O (9:1). Hydroquinone may be added for distillation.

References

1. (a) Lang, R. W.; Hansen, H.-J. HCA 1980, 63, 438. (b) Lang, R. W.; Hansen, H.-J. OS 1984, 62, 202
2. Hamlet, Z.; Barker, W. D. S 1970, 543.

Raw materials

Preparation Products