4-Toluenesulfonyl chloride → 2-[5-(4-Cyanophenyl)-1-benzofuran-2-yl]ethyl 4-methylbenzenesulfonate

Participants

Reaction Steps

The product from Example 1B (2.03 kg, 7.71 mol) in acetonitrile (31.8 kg) was treated in succession with triethylamine (1.86 kg, 18.34 mol), 4-(dimethylamino)pyridine 0.10 kg, 0.87 mol), and p-toluenesulfonyl chloride (3.50 kg, 17.99 mol). After stirring at room temperature for about 5 hours, the reaction mixture was distilled to a minimum volume and treated with isopropyl alcohol (24.1 kg). The suspension was heated at about 30° C. for 1 hour, then cooled to about 5° C., filtered, and the filter cake was washed with isopropyl alcohol (5.20 kg). The solid was dried at 50° C. to provide 2.59 kg (80% yield) of the title compound. MS-DCI (M+NH4)+ m/z at 435; 1H NMR (CDCl3 at 400 MHz) δ 2.38 (s, 3H), 3.15 (t, 2H), 4.38 (t, 2H), 6.50 (s, 1H) 7.18-7.24 (m, 2H), 7.37-7.46 (m, 2H), 7.67-7.74 (m, 7H); 13C NMR (CDCl3 at 100 MHz) δ 21.9, 28.9, 67.2, 104.4, 110.3, 111.2, 118.7, 119.2, 123.0,127.5, 127.6, 129.0, 129.4, 132.2, 132.4, 133.9, 144.4, 145.7, 154.1, 154.5.

Provenance & Evidence