Triethylamine → HCID 53940889, compound

Participants

Reaction Conditions

Reaction Steps

(3-Trifluoromethylphenyl)acetic acid (25.1 g, 0.12 mol) is added to a solution of dichloromethane (200 ml) and dimethylformamide (1 ml). Thionyl chloride (18.2 g, 0.15 mol) is then added dropwise and the resulting solution is stirred overnight. The solution is then concentrated under reduced pressure to give the crude acid chloride in nearly quantitative yield. The potassium salt of ethyl malonate (41.3 g, 0.24 mmol) is dissolved in acetonitrile (400 ml) and is cooled to 0° C. Triethylamine (23.23 g, 0.23 mol) and magnesium chloride(28.8 g, 0.30 mol) are then added and the slurry is warmed to 25° C. and is stirred for 2 hours. The slurry then is cooled to 0° C. and the acid chloride is added over 1 hour. The mixture is allowed to warm to room temperature and is stirred overnight. The solvent is removed under reduced pressure and the resulting solid is suspended in toluene (200 ml) and is cooled to 0° C. Ice cold 4N hydrochloric acid is then slowly added. The organic phase is separated and washed with 4N hydrochloric acid, water and finally saturated brine. The organic phase is dried and concentrated. The crude product is then purified by distillation to give ethyl-(3-trifluoromethylphenyl) acetoacetate (15.4 g).

Provenance & Evidence