Iodine → 5-(1,3-Dioxan-2-yl)-2-iodo-1-methyl-1H-imidazole

Temperatur

-78 °C

To a solution of 38 (295 g, 1.754 mmol) in dry THF (10 mL) at −78° C. was added n-BuLi (0.772 mL, 1.929 mmol, 2.5 M solution in hexanes) and the reaction mixture was stirred for 20 min. Iodine (445 mg, 1.754 mmol) in THF (2 mL) was slowly added dropwise while maintaining the temperature at −78° C. and the reaction mixture was stirred for a further 30 min, and was quenched by the addition of water and then extracted with EtOAc. The organic phase was, washed with sodium thiosulfate solution, separated, dried over Na2SO4, filtered and concentrated. Purification by column chromatography (20% EtOAc/Hexane) afforded 39 (305 mg, 59% yield) as a white solid. MS (m/z): 294.1 (M+H).

1. stirringthe reaction mixture was stirred for a further 30 min
2. customwas quenched by the addition of water
3. extractionextracted with EtOAc
4. washwashed with sodium thiosulfate solution
5. customseparated
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by column chromatography (20% EtOAc/Hexane)

ORD-Eintrag

ord-131c2cab4664488e81423e9518a3816e

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08389541B2