Ethyl chloroformate → 3-(3,4-Dimethoxyphenyl)propanamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(3,4-dimethoxy-phenyl)-propionic acid (10.0 g, 47.6 mmol) in dry THF (175 mL), under nitrogen, is added TEA (7.3 ml, 52.4 mmol). The resulting mixture is cooled to −10° C. before ethyl chloroformate (5.0 ml, 52 mmol) is added dropwise. After stirring at −10° C. (20 min), ammonium hydroxide (25% in water, 105 ml) in THF (105 mL) is added and the mixture is stirred at −15° C. for 30 min and then at rt for 1.5 h. The reaction mixture is concentrated in vacuo, extracted three times with CH2Cl2 and the combined organic extracts are washed with saturated aqueous NaHCO3 and brine. The organic phase is dried over anhydrous MgSO4, filtered and concentrated to give the title compound as a colorless solid.

Provenance & Evidence