Reaction Steps
A mixture of 4-(benzyloxy)-2-(3-chloropropoxy)-5-(thiophen-3-yl)ethylbenzene (1.25 g, 3.23 mmol), 3-(2-cyanophenoxy)-2-propylphenol (0.82 g, 3.2 mmol), potassium iodide (0.21 g, 1.3 mmol), potassium carbonate (1.12 g, 8.08 mmol), and methyl sulfoxide (2 mL) in 2-butanone (10 mL) was refluxed for 60 h. The mixture was cooled to room temperature, diluted with ether, and washed with water. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 5% ethyl acetate/95% hexane) of the residue provided 1.31 g (67%) of the title product as a colorless oil. 1H NMR (CDCl3) δ 7.66 (d, J=7.8. Hz, 1H), 7.57 (d, J=2.9 Hz, 1H), 7.48 (d, J=5.2 Hz, 1H), 7.45-7.25 (m, 8H), 7.20 (t, J=8.2 Hz, 1H), 7.10 (t, J=8.1 Hz, 1H), 6.82 (d, J=8.3 Hz, 1H), 6.77 (d, J=8.6 Hz, 1H), 6.64 (s, 1H), 6.63 (d, J=6.4 Hz, 1H), 5.11 (s, 2H), 4.26 (t, J=6.0 Hz, 2H), 4.22 (t, J=6.0 Hz, 2H), 2.65 (m, 4H), 2.36 (quintet, J=5.9 Hz, 2H), 1.58 (hextet, J=7.5 Hz, 2H), 1.24 (t, J=7.5 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H); MS FD m/e 603 (p); IR (CHCl3, cm−1) 2967, 2250, 1613, 1501. Anal. Calcd for C38H37NO4S: C, 75.59; H, 6.18; N, 2.32. Found: C, 74.65; H, 6.21; N, 2.57.
