2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 135754581, compound

Participants

Reaction Steps

To a stirred solution of the alcohol (6-2, 29 mg, 0.11 mmol) in tetrahydrofuran (2 mL) was added at the ambient temperature 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (75 mg, 0.33 mmol). After 5 h stirring, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. Chromatography (SiO2, 50% ethyl acetate in hexanes) afforded the desired product (6-3) as a light tan solid; 1H NMR (400 MHz, DMSO-d6) δ 13.42 (s, 1H), 11.14 (s, 1H), 9.98 (s, 1H), 8.22 (d, 1H, J=8.4 Hz), 8.20 (s, 1H), 7.70–7.56 (m, 3H), 7.46 (t, 1H, J=7.8 Hz), 7.36 (s, 1H), 7.28 (t, 1H, J=7.8 Hz).

Provenance & Evidence