Imidazole → 7-(Iodomethyl)pentadecane

Temperature

0 °C

Under air, triphenylphosphine (107.44 g, 410 mmol, 1.19 equiv.) and imidazole (28.9 g, 424 mmol, 1.23 equiv.) were dissolved in dichloromethane (800 mL). 2-Hexyl-1-decanol (100 mL, 345 mmol., 1.00 equiv.) was added to the solution, and the reaction mixture was cooled to 0° C. Iodine (103.6 g, 408 mmol., 1.18 equiv.) was added portion-wise over 1 hour, after which the suspension was stirred at 0° C. for an additional hour, and then at ambient temperature for 18 hours. The mixture was quenched with saturated aqueous Na2SO3 (150 mL), and DCM was removed in vacuo. Hexane (200 mL) was added to the residue, and the mixture was filtered to remove salts that had precipitated. The organic material was extracted with hexanes (3×300 mL), dried over Na2SO4, filtered through a pad of silica gel, and then concentrated in vacuo to give a clear, colorless oil (97.8 g, 82% yield). 1H NMR (500 MHz, CDCl3) δ 3.28 (d, J=4.6 Hz, 2H), 1.34-1.19 (m, 24H), 1.12 (b, 1H), 0.91-0.87 (m, 6H).

1. customThe mixture was quenched with saturated aqueous Na2SO3 (150 mL), and DCM
2. customwas removed in vacuo
3. additionHexane (200 mL) was added to the residue
4. filtrationthe mixture was filtered
5. customto remove salts that
6. customhad precipitated
7. extractionThe organic material was extracted with hexanes (3×300 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered through a pad of silica gel
10. concentrationconcentrated in vacuo

ORD record

ord-4c2cef528ef4430fb4a886252a8c0b33

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09312492B2