Cornforth reagent → 1-(1H-indazol-6-yl)ethan-1-one
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]([OH:12])[CH3:11])[CH:8]=2)[CH:3]=[N:2]1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>CC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10](=[O:12])[CH3:11])[CH:8]=2)[CH:3]=[N:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-(1H-indazol-6-yl)ethanol (100 mg, 0.6 mmol) in acetone (50 mL) was added PDC (1.11 g, 3 mmol). The mixture was stirred overnight at rt. The mixture was filtered through silica gel and purified by silica gel chromatography (4:1 EtOAc/Hex) to give the title compound as a brown solid (70 mg, 72%). 1H NMR (400 MHz, CDCl3) δ 8.45 (s, 1H), 8.23 (s, 1H), 8.09-8.08 (m, 1H), 7.56-7.54 (m, 1H), 2.72 (s, 3H).