Triethylamine → HCID 67238429, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottomed flask, charged with 1-(4-(trifluoromethyl)phenyl)pentane-1,4-dione (3.18 g, 13.02 mmol) in EtOH (Ratio: 2, Volume: 13 mL) and ethyl 2-aminoacetate hydrochloride (1.818 g, 13.02 mmol) was added ethyl 2-aminoacetate hydrochloride (1.818 g, 13.02 mmol) and triethylamine (10.53 mL, 76 mmol). The reaction mixture was heated at 70° C. for 15.5 h (˜50% of SM remained by TLC and LCMS). The reaction was then concentrated and the residue was treated with water and extracted with DCM (3×). The organic layer was dried with MgSO4. The crude product was added to a 120 g ISCO silica gel column and was purified with a gradient of 0% to 50% EtOAc/hexanes. The product was obtained as a light yellow oil (1.8 g, 5.98 mmol, 45.9% yield). 1H NMR (CDCl3/400 MHz) δ (ppm) 7.62 (d, 2H), 7.42 (d, 2H), 6.23 (d, 1H), 6.05-6.02 (m, 1H), 4.55 (s, 2H), 4.25 (q, 2H), 2.24 (s, 3H), 1.28 (t, 3H). MS m/z: 312.22 (M+1).

Provenance & Evidence