Potassium Carbonate → HCID 42599389, compound

HRID 1898717Notes

Reaction equation

HRID 1898717 reaction equation
[OH:1][C:2]1[C:3]([CH3:25])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:24])([C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[O:15])[CH2:6][CH2:5]2.[O:26]=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C([O-])(O)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C(C#N)(C)=O.CCOC(C)=O>[OH:26][C:7]([CH3:24])([CH2:6][CH2:5][C:4]1[C:9](=[O:8])[C:10]([CH3:13])=[C:11]([CH3:12])[C:2](=[O:1])[C:3]=1[CH3:25])[C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[O:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 21737544HCID 21737544, compound

Product 1

HCID 42599389HCID 42599389, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 694302-OxopropiononitrileSolvent

Procedure

A solution of 6-hydroxy-2,5,7,8-tetramethyl-N-(pyridin-2-ylmethyl)chroman-2-carboxamide (104 mg, 0.307 mmol) in 4 mL AcCN was chilled to 0° C. and CAN (370 mg in 2 mL H2O) added followed by 8 mL EtOAc, 4 mL 1.0 M NaHCO3 and 250 mg K2CO3. The emulsion was extracted 5×4 mL EtOAc and the combined organics washed 2×4 mL saturated NaCl, dried over Na2SO4 and concentrated to yellow oil. Flash chromatography yielded 2-hydroxy-2-methyl-N-(pyridin-2-ylmethyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide.

Workup

  1. extractionThe emulsion was extracted 5×4 mL EtOAc
  2. washthe combined organics washed 2×4 mL saturated NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to yellow oil

Sources & evidence

ORD record
ord-edecc1a2f6b444b7b7deca8839f685a2
Source dataset
uspto-grants-2013_08
Patent number
US08519001B2

Reaction notes

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