Sodium Iodide → 8-(Iodomethyl)-1,4-dioxaspiro[4.5]decane

Temperature

25 °C

A solution of (1,4-dioxa-spiro[4.5]dec-8-yl)-methanol (1.60 g, 9.29 mmol) in methylene chloride (50 mL) was treated with 4-(dimethylamino)pyridine (1.26 g, 10.22 mmol) and p-toluenesulfonyl chloride (1.86 g, 9.75 mmol). The reaction mixture was stirred at 25° C. for 2 h, and was then washed with a saturated aqueous sodium bicarbonate solution (1×25 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was dissolved in acetone (30 mL) and treated with sodium iodide (4.73 g, 31.53 mmol). The reaction was heated under reflux for 2 h, cooled to 25° C., and then concentrated in vacuo. The resulting residue was suspended in ethyl acetate (50 mL), washed with water (2×15 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 19/1 hexanes/ethyl acetate) afforded 8-iodomethyl-1,4-dioxa-spiro[4.5]decane (2.32 g, 88.6%) as a colorless oil.

1. washwas then washed with a saturated aqueous sodium bicarbonate solution (1×25 mL)
2. dry with materialThe organic layer was dried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. dissolutionThe resulting oil was dissolved in acetone (30 mL)
6. temperatureThe reaction was heated
7. temperatureunder reflux for 2 h
8. temperaturecooled to 25° C.
9. concentrationconcentrated in vacuo
10. washwashed with water (2×15 mL)
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated in vacuo

ORD record

ord-e38555b2448b4740bbadd2770d5c1c23

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259166B2