Chloroform → 3-(1H-Imidazol-1-ylmethyl)-5-[(4-methoxyphenoxy)methyl]-2-methyl-3-(2-naphthalenyl)isoxazolidine

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A mixture of compound 2 (13.0 g, 0.049 mol) and p-methoxyphenyl allyl ether (12.07 g, 0.073 mol) in 400 ml of toluene is refluxed for 48 hours, cooled, and the solvent removed in vacuo leaving a dark oil. Chloroform is added to the oil and carbon is added to decolorize the solution which is filtered through a bed of celite. The chloroform is evaporated and the oil that remained is purified by flash chromatography on silica gel (eluent comprised of 98% CHCl3 and 2% MeOH). The resulting tan solid (5.56 g, 26%) is recrystallized from ethyl acetate, m.p. 143°-145° C. (Found: C, 72.58; H, 6.46; N, 9.66. C26H27N3O3 requires: C, 72.71; H, 6.34; N, 9.78).

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