Water → E,E-1-(p-isopropylphenyl)-5-(2-thienyl)-1,4-pentadien-3-one

Participants

Reaction Steps

A mixture of 7.9 grams (0.042 mol) of E-4-(p-isopropylphenyl)-3-butene-2-one, 4.7 grams (0.042 mol) of 2-thiophene carboxaldehyde, 2mL of 10% sodium hydroxide, 30 mL of water, and 75 mL of ethanol was stirred at ambient temperature for 15 hours. The product was collected by filtration and air dried to give 10.2 grams (86% of theoretical yield) of E,E-1-(p-isopropylphenyl)-5-(2-thienyl)-1,4-pentadien-3-one as a yellow solid. Melting point was determined to be 100°-101° C. Proton nuclear magnetic resonance (1H NMR) was conducted in CDCl3: d 7.84 (d, 1H, J=16 Hz), 7.69 (d, 1H, J=16 Hz), 7.53 (AA'BB', 2H), 7.39 (m, 1H), 7.32 (m, 1H), 7.25 (AA'BB', 2H), 7.06 (dxd, 1H, J=3.6, 5 Hz), 6.96 (d, 1H, J=16 Hz), 6.87 (d, 1H, J=16 Hz), 2.90 (septet, 1H, J=7 Hz), 1.23 (d, 6H, J=7 Hz). Infrared spectroscopy was conducted using a KBr pellet: 2960, 1650, 1585, 1180, and 705 cm-1. Field desorption mass spectral analysis (FDMS) was consistent with the proposed formula (C18H18 0S) m+ /z 316.

Provenance & Evidence