Benzenepropanoic acid → HCID 54709996, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (1.12 ml; 8 mmol; Aldrich) was added to 4-hydroxy-6-methyl-2-pyrone (1.01 g; 8 mmol; Aldrich) in 60 ml CH2Cl2, and the reaction mixture was stirred under N2 for 10 min at 0° C. DMAP (293.3 mg; 2.4 mmol; Aldrich) and DCC (1.65 g; 8 mmol; Aldrich) were added, and the reaction mixture was stirred under N2 for 15 min at 0° C. Hydrocinnamic acid (1.20 g; 8 mmol; Aldrich) was added, and the reaction mixture was stirred N2 for 12 h at room temperature. The reaction mixture was filtered on celite to remove urea, acidified to pH ˜2 by addition of by 1 N HCl, diluted by addition of 60 ml water was added, and extracted with CH2Cl2 (2×100 ml). The organic layer was washed with brine, dried over anhydrous Na2SO4, and evaporated under vacuum. The product was isolated by chromatography on silica gel. Yield: 58%. MS (MALDI): calculated, m/z 259.1 (MH+); found, 259.1.

Provenance & Evidence