Acetone → HCID 89545285, compound

Participants

Reaction Steps

90 mg of 40 (0.33 mmol) was dissolved in 5 ml of acetone at room temperature. To this solution was added 359 mg of DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) (1.58 mmol) in one portion. The reaction mixture immediately turned color from blue to red as it was stirred in the dark for 1 hour. When all reactant was gone the reaction mixture was stirred with 15 ml of saturated sodium thiosulfate solution to remove unreacted DDQ for 2 min and then 15 ml of saturated sodium bicarbonate was added, and then it was stirred for 2 min to remove acidic DDQH2. The reaction mixture was then extracted with chloroform (5×40 ml). The combined bottom red organic phases were subsequently washed with 15 ml of saturated NaCl solution, dried over anhydrous MgSO4, filtered and evaporated. The red residue was then purified by column chromatography using 7:3 hexane:ethylacetate to provide 88.4 mg of bis-aldehyde 32 in 89% yield as red crystals. 1H NMR δ 10.59 (s, 2H), 10.12 (dd, 2H, J=10), 8.11 (tt, 1H, J=10), 7.94 (t, 1H, J=10), 1.05 (s, 9H), 0.61 (s, 6H); 13C NMR δ 190.28, 162.4, 144.9, 142.75, 140.94, 134.14, 132.73, 27.06, 17.99, 0.98; LRMS (LC/MS-ESI, MeOH) m/e 299 (MH+)

Provenance & Evidence