4-Chlorostyrene → 5-(4-Chlorophenyl)-3-(2-furanyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidine

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Reaction Steps

A solution of 7.60 g (0.037 mol) of 1-(2-furanyl)-2-(1H-imidazol-1-yl)-N-methylethanimine N-oxide (4) and 7.70 g (0.056 mol) of 4-chlorostyrene in 400 ml of toluene is refluxed for 48 hours under a nitrogen atmosphere. Upon cooling to ambient temperature, the crude cis- and trans-diastereomeric mixture of compound 6 (R=C6H4Cl--4) is concentrated in vacuo and flash-chromatographed on neutral silica gel using a 98:2 by volume mixture of chloroform and methanol to give 1.30 g (10%) of isomer A, melting point 99°-101° C. (ethyl acetate-hexane, 1:1 by volume). Anal. Calcd. for C18H18ClN3O2 : C, 62.88; H, 5.28; Cl, 10.31; N, 12.22 Found: C, 62.90; H, 5.39; Cl, 10.44; N, 12,13. Isomer B (1.10 g, 8.5%) has a melting point of 131°-133° C. (ethyl acetate-hexane, 1:1 by volume). Anal. Calcd. for C18H18ClN3O2 : C, 62.88; H, 5.28; Cl, 10.31; N, 12.22. Found: C, 62.82; H, 5.28; Cl, 10.46; N, 12.12.

Provenance & Evidence