1,1'-Azobis(cyclohexanecarbonitrile) → HCID 56605006, compound

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Reaction Steps

To a solution of compound 34b (1.24 g, 1.0 eq.) in toluene (12 mL) was added tris(trimethylsilyl)silane (1.48 mL, 1.2 eq.) with stirring, followed addition of 1,1′-azobis(cyclohexanecarbonitrile) (AIBN) (98 mg, 0.1 eq.). The reaction mixture was stirred at 90° C. for 1.5 hrs. The solution was cooled down to room temperature, quenched with 5% citric acid solution, and extracted with EtOAc (50 mL). Organics were washed sequentially with H2O (30 mL), saturated NaHCO3 aqueous solution (30 mL), and brine (30 mL), and concentrated under reduced pressure to yield a colourless oil. Crude material was purified by chromatography on silica gel (petroleum ether/EtOAc) to yield compound 34c as white crystals in 71% yield. 1H NMR (CDCl3, 400 MHz) δ 1.68-1.73 (m, 4H), 2.05-2.18 (m, 2H), 2.82-2.85 (m, 2H), 3.60 (s, 3H), 4.71 (m, 1H).

Provenance & Evidence