Sodium Iodide → 2-(3-iodopropoxy)tetrahydro-2H-pyran

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2-(3′-Chloropropoxy) tetrahydro-2H-pyran (Aldrich) (9 g, 0.05 mol) was added to a solution of sodium iodide (37.8 g, 0.25 mol) in acetone (250 mL) with stirring. The resultant slurry was refluxed for 48 hours. The mixture was cooled, evaporated to a solid mass and transferred to the top of a short column of neutral alumina. The column was washed with CH2Cl2 (1 L) and CH2Cl2 was removed using a rotary evaporator. The product was obtained as yellow liquid (12.6 g, 93%). 1H NMR δ: 1.62-1.86 (m, 6 H, ring CH2), 2.07 (m, 2 H, CH2—CH2—I), 3.27 (m, 2 H, CH2—I), 3.38-3.54 (m, 2 H, CH2—O), 3.74-3.89 (m, 2 H ring O—CH2), 4.58 (t, 1 H, J=3.2 Hz, ring CH); λmax/nm (εmax/dm3 mol−1 cm−1) 267 (1500); HRMS (EI+) calc. for C8H15IO2: 269.0049. found 269.0039.

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