Water → HCID 59442520, compound

Participants

Reaction Conditions

Reaction Steps

4.7 g (118 mmol) of sodium hydride (60% strength in mineral oil) were washed with pentane under a nitrogen atmosphere, suspended in 100 ml of DMF and cooled to 0° C. A solution of 12.5 g (107 mmol) of 5-chloro-4-methyl-1H-imidazole in 100 ml of DMF was added. Then 5.5 g of bromomethylcyclopropane were added and the mixture was stirred for 16 h at 20° C. 250 ml of water and EA were added, the phases were separated and the aqueous layer was extracted with EA. The combined organic phases were washed with brine and dried over sodium sulfate. The solvent was removed in vacuo. Flash chromatography (silica gel; EA/HEP, gradient from 20:80 to 40:60) of the residue yielded 7.5 g of 4-chloro-1-cyclopropylmethyl-5-methyl-1H-imidazole as an oil and 3.6 g of 5-chloro-1-cyclopropylmethyl-4-methyl-1H-imidazole as an oil.

Provenance & Evidence