Dimethylformamide dimethyl acetal → 3-Dimethylamino-2-(furan-2-carbonyl)-acrylic acid ethyl ester

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Reaction Steps

Following the method of Menozzi et al. (J. Heterocyclic Chem. 1987, 24, 1669), a mixture of 5.3 g (29.1 mmol) ethyl beta-oxo-2-furanpropionate and 7.7 ml (57.8 mmol) N,N-dimethylformamide dimethyl acetal was stirred for 6.5 hours at room temperature. The reaction mixture was then concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was dried with sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) afforded 3.6 g (52%) 3-dimethylamino-2-(furan-2-carbonyl)-acrylic acid ethyl ester as a yellow oil. EI-MS m/e (%): 237 (M+, 36), 163 ([M—EtOH—CO]+, 100), 95 (86).

Provenance & Evidence