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General procedure. To a mixture of homoallyl alcohol (1 mmol) and aldehyde (1 mmol, CeCl3 · 7H2O (1.0mmol) and LiI (1.5 mmol) in dichloroethane (5 mL) was stirred at reflux temperature for a specified time as required to complete the reaction (Table 1, After complete conversion, as indicated by TLC, the reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (2 × 10mL, The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo and purified by column chromatography on silica gel (Merck, 100-200 mesh, ethyl acetate-hexane, 1:9) to afford the pure 4-iodotetrahydropyran. The products thus obtained were characterized by IR, NMR spectroscopy, and physical constants. The characterization data was found to be consistent with the authentic samples
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4, concentrated in vacuo and purified by column chromatography on silica gel (Merck, 100-200 mesh, ethyl acetate-hexane, 1:9) to afford the pure 4-iodotetrahydropyran. The products thus obtained were characterized by IR, NMR spectroscopy, and physical constants. The characterization data was found to be consistent with the authentic samples.
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