2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57523622, compound

Participants

Reaction Steps

A solution of 5-methyl-2-oxo-5-((trimethylsilyl)ethynyl)cyclohexane-carbonitrile (270 mg) and DDQ (350 mg) in benzene (20 mL) was heated under reflux for 10 min. After removal of insoluble matter, the filtrate was concentrated in vacuo to give a residue (407 mg). The residue was purified by flash chromatography [hexanes-ethyl acetate (4:1)] to give 10 as a crystalline solid (142 mg, 78%): 1H NMR (acetone-d6) δ 7.71 (1H, d, J=1.5 Hz), 2.72 (1H, m), 2.62 (1H, m), 2.21 (2H, m), 1.55 (3H, s), 0.15 (9H, s); 13C NMR (acetone-d6) δ 192.0, 164.8, 116.4, 114.8, 106.5, 88.7, 35.9, 35.0, 0.0.

Provenance & Evidence