Trimethylsilyl iodide → [1-(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydronaphthalen-1-yl]methyl Acetate

Participants

Reaction Steps

To a solution of Example 179C (0.12 g, 0.38 mmol) in acetonitrile (3.5 mL) was added iodotrimethylsilane (TMSI) (81 μL, 0.57 mmol). The reaction solution was stirred at room temperature for 3 h. After which, additional 1.5 equivalents of TMSI (81 μL) were added and stirring was continued for 2 h. The solution was quenched with water (3 mL) and extracted with ethyl acetate (2×5 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (70% ethyl acetate/hexane) afforded product as a white solid (91%). 1H NMR (300 MHz, CDCl3) δ ppm 0.55 (s, 1 H), 0.77 (m, 12 H), 0.93 (m, 2 H), 1.36 (m, 3 H), 1.79 (m, 8 H), 2.19 (m, 3 H), 3.77 (m, 2 H), 4.42 (d, J=11.03 Hz, 1 H), 4.57 (m, 3 H), 6.15 (s, 1 H), 7.46 (m, 4 H), 7.59 (m, 1 H), 7.69 (m, 1 H), 8.12 (m, 2 H); MS m/z 303.0.

Provenance & Evidence