4-Methylmorpholine → 5-(4-Trifluoromethoxy-phenyl)-pent-4-ynoic acid methoxy-methyl-amide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(4-trifluoromethoxy-phenyl)-pent-4-ynoic acid (1.0 g, 3.87 mmol; example 10 b]) in CH2Cl2 (50 ml) was added N,O-dimethylhydroxylamine hydrochloride (0.45 g, 4.65 mmol) and N-methylmorpholine (0.55 ml, 5 mmol). The mixture was cooled to 0° C. and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.97 g, 5 mmol) was added. The reaction solution was naturally warmed to ambient temperature, stirred over night and partitioned between aqueous 10% KHSO4/ether (three times). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl and dried (Na2SO4) to give 1.165 g (3.86 mmol, quant.) of the title compound as brown oil.

Provenance & Evidence