Cornforth reagent → 1-(1H-indazol-6-yl)ethan-1-one

HRID 1615258Notes

Reaction equation

HRID 1615258 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]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 687611451-(1H-Indazol-6-yl)ethanol

Product 1

HCID 441192231-(1H-indazol-6-yl)ethan-1-oneYield 72.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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).

Workup

  1. filtrationThe mixture was filtered through silica gel
  2. custompurified by silica gel chromatography (4:1 EtOAc/Hex)

Sources & evidence

ORD record
ord-b5ff004fbcdb43ad8fd567e892e8c00b
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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