[I:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4]1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[I:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([O:8][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:9]2)[CH2:4]1A solution of 3-iodomethyl-cyclopentanol (7.71 g, 34.10 mmol) in methylene chloride (171 mL) was treated with 3,4-dihydro-2H-pyran (4.7 ml, 51.16 mmol) and pyridinium p-toluenesulfonate (857.1 mg, 3.41 mmol). The resulting reaction mixture was stirred at 25° C. for 24 h. The reaction mixture was then washed with a saturated aqueous sodium chloride solution (1×200 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 19/1 petroleum ether/diethyl ether) afforded 2-(3-iodomethyl-cyclopentyloxy)-tetrahydropyran (7.91 g, 75%) as a yellow oil: EI-HRMS m/e calcd for C11H19IO2 (M+) 310.0430, found 310.0433.
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