Ethyl bromoacetate → ethyl [6-cyano-1-(1-trityl-1H-imidazol-4-yl)-1,2,3,4-tetrahydronaphthalen-1-yloxy]acetate

Participants

Reaction Steps

1.9 mmol of sodium hydride (60% dispersion in oil) are added in portions to a solution of 1.3 mmol of 5-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile in 10 ml of tetrahydrofuran, and the mixture is stirred under reflux for 1 hour. 3.0 mmol of ethyl bromoacetate [105-36-2] are added and the reaction mixture is stirred under reflux for 8-16 hours. The reaction mixture is cooled and poured into saturated sodium bicarbonate solution and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of its Rf by flash chromatography (SiO2 60F).

Provenance & Evidence