2-IODOMETHYL-1,4-DIOXANE synthesis

Yield:64179-17-5 85%

Reaction Conditions:

with iodine;sodium hydrogencarbonate in acetonitrile at 20; for 20 h;

Steps:

62.a

(62a) 2-iodomethyl-1,4-dioxane To an acetonitrile (420 mL) solution of 2-(allyloxy)ethanol (14 g, 137 mmol), sodium hydrogen carbonate (34.6 g, 410 mmol) and iodine (104 g, 410 mmol) were added and stirred at room temperature for 20 hours. To the reaction mixture, water was added and was extracted with ethyl acetate. Thereafter, the organic layer was washed with an aqueous sodium thiosulfate solution and a saturated saline solution, dried over magnesium sulfate, and filtrated through a silica gel column pad, and the filtrate was concentrated to obtain the title compound (26.5 g, yield 85%) as a yellow liquid. ¹H NMR(400 MHz, CDCl₃) δppm; 3.10(2H, d, J=8 Hz), 3.34(1H, dd, J=8, 13 Hz), 3.66-3.98 (6H, m).

References:

US2007/10542,2007,A1 Location in patent:Page/Page column 80