Triacetoxyperiodinane → HCID 86732728, compound

HRID 525862Notes

Reaction equation

HRID 525862 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[CH:8]=[C:7]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:6]2=[O:24].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][C:7]2[C:6](=[O:24])[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([CH:2]=[O:1])[CH:4]=3)[N:9]([CH3:13])[CH:8]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86732729HCID 86732729, compound

Product 1

HCID 86732728HCID 86732728, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-(hydroxymethyl)-3-((4-methoxybenzyl)oxy)-1-methylquinolin-4(1H)-one (1.5 g, 4.61 mmol) in dichloromethane (DCM) (80 mL) at room temperature was added Dess-Martin periodinane (2.347 g, 5.53 mmol). The reaction mixture soon turned into a clear brown solution and was stirred at room temperature for 1 h. Saturated sodium bicarbonate solution was then added, and the mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by automatic silica gel column chromatography (Combiflash RF) eluting with ethyl acetate/hexanes (0-100%) to afford 3-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydroquinoline-6-carbaldehyde (1.1 g, 3.40 mmol, 73.8% yield) as a yellow solid. LCMS: (M+H)+: 324.0

Workup

  1. extractionthe mixture was extracted 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. customThe residue was purified by automatic silica gel column chromatography (Combiflash RF)
  7. washeluting with ethyl acetate/hexanes (0-100%)

Sources & evidence

ORD record
ord-cf3b9113e9e44012a11f3a7b4cfe1d6a
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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