Trimethylsilyl iodide → Methyl 1-(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydronaphthalene-1-carboxylate

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Reaction Steps

To a solution of Example 178B (0.18 g, 0.6 mmol) in acetonitrile (2 mL) was added iodotrimethylsilane (TMSI) (0.13 mL, 0.9 mmol). The reaction solution was stirred at room temperature for 3 h. After which, additional 1.5 equivalents of TMSI (0.13 mL) were added and stirring was continued for 2 h. The solution was quenched with water (5 mL) and extracted with ethyl acetate (2×5 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (40%-80% ethyl acetate/hexane) afforded product as a white solid (0.11 g, 65%). 1H NMR (300 MHz, CDCl3) δ ppm 0.46 (m, 1 H), 0.79 (m, 7 H), 1.41 (m, 1 H), 2.29 (m, 1 H), 2.53 (m, 1 H), 3.60 (s, 3 H), 3.83 (m, 1 H), 6.11 (s, 1 H), 7.52 (m, 3 H), 8.12 (d, J=7.72 Hz, 1 H); MS m/z 289.0 (M+H)+.

Provenance & Evidence