Tin tetrachloride → 2-{[1-Methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

Participants

Reaction Steps

Following the procedure described in Step 2 of Example 1, 2-{[6-(1-benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}acetonitrile (1.15 g, 3.67 mmol) was acylated with valeryl chloride (0.52 mL, 4.4 mmol), in presence of tin (IV) chloride (0.52 mL, 4.4 mmol) in methylene chloride (15 mL). 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile was prepared. Purification by flash chromatography (Biotage apparatus) using 10-20% chloroform in hexane and 100% hexane and 0.5-5% ethyl acetate in hexane as eluants yielded the title compound as a yellow gum (0.458 g). 1HNMR (300 MHz, DMSO-d6): δ8.45 (s, 1H), 8.2 (d, 1H, J=7.7 Hz), 8.05 (t, 2H, J=8.8 Hz), 7.95 (d, 1H, J=7.7 Hz), 7.75 (d, 1H, J=7.7 Hz), 8.65 (d, 1H, J=7.7 Hz), 7.4-7.5 (m, 2H), 5.35 (s, 2H), 2.75 (t, 2H, J=8.1 Hz), 2.55 (s, 3H), 1.5-1.6 (m, 2H), 1.1-1.25 (m, 2H), and 0.7 ppm (t, 3H, J=8.8 Hz).

Provenance & Evidence