Triacetoxyperiodinane → HCID 86613893, compound

HRID 598162Notes

Reaction equation

HRID 598162 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[CH3:25])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:26])[C:10]([CH2:27][OH:28])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(=O)(O)[O-].[Na+]>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[CH3:25])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:26])[C:10]([CH:27]=[O:28])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67267345HCID 67267345, compound

Product 1

HCID 86613893HCID 86613893, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To 0.20 g (0.54 mmol) of 1-benzyl-5-(2,4-dimethylphenyl)-3-(hydroxymethyl)cinnolin-4(1H)-one in 10 mL of dichloromethane was added 0.28 g (0.65 mmol) of Dess-Martin periodinane. The reaction was stirred at room temperature for 90 min before being diluted with sodium bicarbonate solution and extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, concentrated in vacuo and purified by flash chromatography eluting with a 33% ethyl acetate/hexanes mixture to give 0.17 g (85%) of the title compound as a yellow powder.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography
  7. washeluting with a 33% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-68a911a28c9c4945bb28d7178f018fad
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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