2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 69752497, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Step B (0.11 g, 0.23 mmol) in 1,4-dioxane (10 mL) was added DDQ (0.19 g, 0.8 mmol) and the solution stirred at 23° C. for 72 h. The solution was poured into aqueous NaHCO3 and the mixture was extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated to a residue, which was purified by chromatography (silica, 25% ethyl acetate in hexanes) to give an oil (0.1 g, 91%): 1H NMR (CDCl3) δ 8.5 (bs, 1H), 8.01 (s, 1H), 7.75 (d, J=6 Hz, 2H), 7.63 (d, J=12 Hz, 1H), 7.5 (bs, 1H), 7.4 (m, 3H), 7.3-7.2 (m, 5H), 5.2 (m, 1H), 5.0 (m, 1H), 4.75 (m, 1H), 4.4-4.3 (m, 2H), 4.1 (m, 1H), 3.93 (s, 3H), 1.21 (t, J=6 Hz, 3H); MS m/z 478 [M+H]+.

Provenance & Evidence