Acetic Acid → HCID 22993835, compound

Participants

Reaction Steps

A solution of the 2-methoxy-4,5-methylenedioxy benzaldehyde (16.00 g, 0.089 mol), diethyl malonate (15.00 mL, 0.090 mol), piperidine (4.40 mL, 0.044 mol) and acetic acid (2.50 mL, 0.045 mol) in benzene (75 mL) stirred at reflux, equipped with a Dean-Stark apparatus, for 24 h. Upon removal of the solvent the crude residue was extracted with ethyl acetate and washed with 10% sodium carbonate solution, water, dried (Na2SO4). After removing the solvent, flash chromatography of the residue (silica gel, 25% ethyl acetate/hexane) provided the title compound as a yellow solid (26.00 g, 91%): 1H NMR (250 MHz, CDCl3) δ 8.50 (s, 1H), 7.45 (d, J=10 Hz, 1H), 7.10 (d, J=15 Hz, 1H), 5.85 (s, 2H), 4.15 (q, 4H), 3.40 (s, 3H), 1.20 (m, 6H); mp: 118° C.

Provenance & Evidence