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

Participants

Reaction Steps

To a mixture of ethyl 2-{[6-(1-benzofuran-2-yl)-1-methyl-2-naphthyl]oxy}-3-phenylpropanoate (0.944 g, 2.10 mmol) in methylene chloride (4.2 mL) at −78° C. was added valeryl chloride (0.25 mL, 2.1 mmol), and tin (IV) chloride (0.25 mL, 2.1 mmol). The reaction mixture was stirred for 2 hours and 20 minutes. It was diluted with extra methylene chloride and poured into excess sodium bicarbonate solution. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The compound was purified by flash chromatography using 100% hexane and 0.5-3% ethyl acetate in hexane. It was dried at 60° C. for 30 minutes to afford ethyl 2-{[1-methyl-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a yellow gum (0.553 g). Mass spectrum (+ESI, [M+H]+) m/z 5351HNMR (500 MHz, DMSO-d6): δ8.35 (d, 1H, J=1.7 Hz), 8.1 (d, 1H, J=9.0 Hz), 8.05 (dd, 1H, J=7.6 Hz and 1.0 Hz), 7.9 (d, 1H, J=9.2 Hz), 7.85 (dd, 1H, J=8.9 Hz and 1.8 Hz), 7.75 (d, 1H, J=8.1 Hz), 7.25-7.45 (m, 8H), 5.3-5.35 (m, 1H), 4.1 (q, 2H, J=6.9 Hz), 3.25-3.35 (m, 2H), 2.75 (t, 2H, J=7.3 Hz), 2.5 (s, 3H), 1.5-1.6 (m, 2H), 1.05-1.2 (m, 5H), and 0.7 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C35H34O5: Calculated: C, 78.63; H, 6.41; N, 0.00. Found: C, 78.70; H, 6.30; N, 0.00.

Provenance & Evidence