Methyl iodide → HCID 53965613, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(triphenylmethyl)-1H-imidazol-4-ylacetic acid methyl ester (1.01 g, 2.63 mmol) in THF (25 ml) was cooled to -78° C. Lithium hexamethyldisilazide (2.76 ml of a 1M solution in THF, 2.76 mmol) was added dropwise and the reaction stirred 30 min at -78° C. Methyl iodide (0.164 ml, 2.76 mmol) was added and the reaction stirred a furthur 1 hr at -78° C. and then at -20° C. for 4 hrs. The reaction was quenched with water (10 ml) and saturated NaHCO3 solutuon (10 ml) and extracted with EtOAc. The organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. Chromatography of the residue (SiO2, 2 to 3% MeOH in CH2Cl2, gradient elotion) afforded the product.

Provenance & Evidence