Trichloroisocyanuric Acid → Furo[2,3-c]pyridine-5-carboxaldehyde

反応式

[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH2:10][OH:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.C1(N(Cl)C(=O)N(Cl)C(=O)N1Cl)=O>CC(C)=O.CC1(C)N([O])C(C)(C)CCC1>[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1

参加物

実験手順

Furo[2,3-c]pyridin-5-yl methanol (521 mg, 3.49 mmol) was dissolved in acetone (17 mL), added 2,2,6,6-tetramethylpiperidine 1-oxyl (27 mg, 170 μmol) at room temperature. Then, the reaction solution was added 1,3,5-trichloro-2,4,6-triazinetrione (892 mg, 3.84 mmol) under ice-cold conditions, and stirred at the same temperature for 5 minutes. The reaction solution was concentrated in vacuo, added water and a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions, extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (488 mg (yield 95%)) was obtained as a yellow solid.