Imidazole → Ethyl 4-iodocyclohexane-1-carboxylate

To a cold (0° C.) stirred solution of 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (1.0 g, 5.80 mmol) in 1:2 CH2Cl2/CCl4 (52 ml) is added triphenylphosphine (1.82 g, 6.96 mmol), imidazole (473 mg, 6.96 mmol), and iodine (1.79 g, 7.08 mmol). The reaction is allowed to warm to room temperature and stirred overnight. The reaction is quenched by the addition of saturated sodium thiosulphate (c.a. 50 ml) and stirred until the solution becomes clear. The layers are separated and the aqueous layer is extracted with CH2Cl2 (3×30 ml). The combined organic phases are washed with sodium thiosulphate (30 ml), brine (30 ml), dried with anhydrous MgSO4, filtered and evaporated at reduced pressure to an oily solid. Purification by dry flash chromatography, Keiselgel 15-40 grade silica, eluting with 3% ethyl acetate/iso hexane yields the title compound as a clear colourless oil.

1. customThe reaction is quenched by the addition of saturated sodium thiosulphate (c.a. 50 ml)
2. stirringstirred until the solution
3. customThe layers are separated
4. extractionthe aqueous layer is extracted with CH2Cl2 (3×30 ml)
5. washThe combined organic phases are washed with sodium thiosulphate (30 ml), brine (30 ml)
6. dry with materialdried with anhydrous MgSO4
7. filtrationfiltered
8. customevaporated at reduced pressure to an oily solid
9. customPurification
10. customby dry flash chromatography, Keiselgel 15-40 grade silica
11. washeluting with 3% ethyl acetate/iso hexane

ORD record

ord-3bfbb0c1e7a445c1b5e17a19d67bcb01

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07273875B2