Ammonium Chloride → HCID 69250022, compound

Participants

Reaction Conditions

Reaction Steps

Cyclopentyl (1-cyclopentyl-1H-imidazol-4-yl)acetate (2.00 g; 7.60 mmol) was dissolved in tetrahydrofuran (THF; 45 ml). The reaction solution was cooled to 0° C. and then lithium hexamethyldisilazane (20% in THF; 6.33 ml; 7.60 mmol) was added dropwise. The mixture was stirred at 0° C. for a further hour. Then methyl cyanoformate (0.66 ml; 8.36 mmol) was added. The mixture was stirred at 0° C. for 10 min and then at RT for 7 h. The reaction solution was then added to saturated NH4Cl solution. It was extracted with EA, and the organic phase was washed with H2O and dried over Na2SO4. The solvent was removed under reduced pressure. Purification of the crude product by column chromatography (120 g of silica gel; EtOAc/n-heptane—2/1) resulted in 0.46 g of cyclopentyl methyl 2-(1-cyclopentyl-1H-imidazol-4-yl)malonate.

Provenance & Evidence