Tin tetrachloride → Ethyl 2-{[1-chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate

Participants

Reaction Steps

Following the procedure described in Step 3 of Example 23, ethyl 2-{[6-(1-benzofuran-2-yl)-1-chloro-2-naphthyl]oxy}acetate (1.90 g, 4.99 mmol) was acylated by valeryl chloride (0.61 mL, 5.1 mmol) in presence of tin (IV) chloride (0.60 mL, 5.1 mmol) in methylene chloride (20 mL). ethyl 2-{[1-chloro-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy} acetate was prepared. Purification by HPLC using 10% tert-butyl methyl ether in hexane as the mobile phase yielded the title compound as a light yellow solid (0.533 g), mp 95-97° C. Mass spectrum (+ESI, [M+H]+) m/z 465. 1HNMR (500 MHz, DMSO-d6): δ8.5 (s, 1H), 8.25 (d, 1H, J=8.9 Hz), 8.15 (d, 1H, J=9.0 Hz), 8.05 (t, 2H, J=8.6 Hz), 7.75 (d, 1H, J=7.8 Hz), 7.55 (d, 1H, J=9.2 Hz), 7.4-7.45 (m, 2H), 5.13 (s, 2H), 4.2 (q, 2H, J=7.0 Hz), 2.75 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.3 (m, 5H), and 0.7 ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C27H25ClO5: Calculated: C, 69.75; H, 5.42; N, 0.00. Found: C, 69.64; H, 5.20; N, 0.01.

Provenance & Evidence