3,4-dihydro-2H-pyran → 2-(3-Iodophenoxy)oxane

Participants

Reaction Steps

The solution of 3-iodophenol (70.31 g), PPTS (750 mg) and 3,4-dihydro-2H-pyran (55.68 g) in CH2Cl2 (400 mL) was refluxed under N2 for 3 h. TLC of the reaction solution indicated the presence of starting material, 3-iodophenol. Consequently, more 3,4-dihydro-2H-pyran (30 mL) and PPTS (350 mg) were added to the reaction solution. The reaction was refluxed for another 3 h. After being cooled to room temperature, the reaction solution was washed by saturated NaHCO3 (100 mL×2), H2O (120 mL×3) and brine (120 mL×1), dried by Na2SO4 and concentrated to give crude product, which was purified to give pure 2-(3-Iodo-phenoxy)-tetrahydro-pyran (89.5 g; 92%). 1H NMR (300 MHz, CDCl3) □ 7.42 (m, 1H), 7.31 (m, 1H), 7.00 (m, 2H), 5.39 (dd, 1H, J=3.0, 3.0 Hz), 3.87 (m, 1H), 3.61 (m, 1H), 1.97 (m, 1H), 1.84 (m, 2H), 1.65 (m, 3H).

Provenance & Evidence