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

To a solution of compound 2 (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 3 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).

1. stirringThe reaction mixture was stirred at 90° C. for 1.5 hrs
2. customquenched with 5% citric acid solution
3. extractionextracted with EtOAc (50 mL)
4. washOrganics were washed sequentially with H2O (30 mL), saturated NaHCO3 aqueous solution (30 mL), and brine (30 mL)
5. concentrationconcentrated under reduced pressure
6. customto yield a colourless oil
7. customCrude material was purified by chromatography on silica gel (petroleum ether/EtOAc)

ORD record

ord-6a62e5ba9ee64d3b97e16c8cf288cea3

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353100B2