Ethyl Acetate → HCID 14994871, compound

Participants

Reaction Steps

A mixture of 2-(4-chlorophenyl)furan (prepared according to A.W. Johnson, J. of Chem. Soc. 1946, p 895-99) (0.105 g), and dimethyl acetylenedicarboxylate (0.07 mL) in distilled water (0.25 mL) was placed in a closed vial and subjected to ultrasonic vibration overnight. The reaction temperature at the end of the reaction was between 40 and 50° C. After cooling the Diels-Alder adduct was isolated by extraction with ethyl acetate. The ethyl acetate extract was dried (Na2SO4) and evaporated to dryness in-vacuo to provide almost pure product which was further purified by chromatography on silica gel using 5-10% acetone in n-hexane. The title compound (0.16 g) m.p. 84° C. was isolated from some of the combined fractions: PMR δH (CDCl3): 3.7(s,3H), 3.84 (s, 3H), 5.76 (d, 1H, J=1.2Hz), 7.58-7.29 (m, 5H).

Provenance & Evidence