Triacetoxyperiodinane → HCID 86645108, compound

HRID 658359Notes

Reaction equation

HRID 658359 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:20])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([CH2:12][OH:13])=[CH:10][CH:11]=1)=[O:5])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:20])[N:8]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:9]([CH:12]=[O:13])=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68497201HCID 68497201, compound

Product 1

HCID 86645108HCID 86645108, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2-dihydro-6-hydroxymethyl-2-oxo-1-phenylpyridine-3-carboxylic acid ethyl ester (5.0 g, 18 mmol) was dissolved in dichloromethane (50 mL), and a DMP reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one) (8.5 g, 20 mol) was added thereto at room temperature. The mixture was allowed to react for 4 hours. The reaction mixture was poured into an aqueous sodium bicarbonate solution, and extracted with chloroform. The organic layer was washed with water, dried, and concentrated, to obtain crude 6-formyl-1-phenyl-1,2-dihydro-2-oxopyridine-3-carboxylic acid ethyl ester. This crude product was dissolved in dichloromethane (50 mL), and a DAST reagent (diethylamino sulfur trifluoride) (4.8 g, 30 mmol) was added to this solution at 5° C. under a nitrogen atmosphere. The mixture was allowed to react overnight at room temperature. The reaction mixture was poured into water, and the organic layer was washed with an aqueous sodium bicarbonate solution and water, dried, and concentrated. Thus obtained residue was purified by column chromatography (elution solvent: hexane/ethyl acetate: 4/1 to 3/2), and thus obtained solid was washed with a mixed solution of hexane/ethyl acetate=1/1, to obtain 2.29 g of a desired product (yield: 57%, two stages).

Workup

  1. customat room temperature
  2. customto react for 4 hours
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea75a50266c74b39a7e25a7afa2d379f
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

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