Imidazole → 7-(Iodomethyl)pentadecane

Temperatur

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-Eintrag

ord-ffb63b48f1d74257833af0c431c70c95

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08883958B2