Tin tetrachloride → 1-[2-(6-Methoxy-2-naphthyl)-1-benzofuran-3-yl]-3-methyl-1-butanone

Participants

Reaction Steps

Following the procedure described in Step 2 of Example 1, 2-(6-methoxy-2-naphthyl)-1-benzofuran (3.00 g, 10.9 mmol), was acylated with isovaleryl chloride (1.9 mL, 16 mmol), in presence of tin (IV) chloride (1.7 mL, 14 mmol) in chloroform (60 mL). Purification by flash chromatography using 15-100% chloroform in hexane as an eluant then by using the Biotage apparatus using 1.5% ethyl acetate in hexane as an eluant yielded the title compound as a yellow wax (1.34 g); 1HNMR (200 MHz, DMSO-d6): δ8.35 (s, 1H), 8.0 (d, 3H, J=8.2 Hz), 7.8 (d, 1H, J=10.2 Hz), 7.7 (d, 1H, J=7.7 Hz), 7.35-7.55 (m, 3H), 7.3 (d, 1H, J=8.7 Hz), 3.95 (s, 3H), 2.6 (d, 2H, J=7.7 Hz), 2.0-2.1 (m, 1H), and 0.75 ppm (d, 6H, J=7.7 Hz).

Provenance & Evidence