Dichloromethane → HCID 42599390, compound

HRID 1898719Notes

Reaction equation

HRID 1898719 reaction equation
[OH:1][C:2]1[C:3]([CH3:26])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:25])([C:14]([NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[O:15])[CH2:6][CH2:5]2.C(Cl)Cl.[O:30]=[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(C#N)(C)=O.O>[OH:30][C:7]([CH3:25])([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[CH3:26])[C:14]([NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[O:15]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 180504Ceric ammonium nitrateHCID 9975437HCID 9975437, compound

Product 1

HCID 42599390HCID 42599390, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 694302-OxopropiononitrileSolvent

Procedure

6-Hydroxy-2,5,7,8-tetramethyl-N-(2-(pyridin-2-yl)ethyl)chroman-2-carboxamide (97.7 mg, 0.276 mmol) was dissolved in 3 mL AcCN and 2 mL CH2Cl2 and cooled to 0° C. prior to treatment with 332.5 mg CAN (0.606 mmol) in 2 mL H2O. The reaction was quenched by the addition of 5 mL EtOAc and 4 mL 1.0 M NaHCO3 followed by extraction of the aqueous layer 3×5 mL EtOAc. The combined organics were back extracted 3×3 mL saturated NaCl, dried over Na2SO4 and concentrated. Flash chromatography yielded 85.8 mg of 2-hydroxy-2-methyl-N-(2-(pyridin-2-yl)ethyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow oil.

Workup

  1. customThe reaction was quenched by the addition of 5 mL EtOAc and 4 mL 1.0 M NaHCO3
  2. extractionfollowed by extraction of the aqueous layer 3×5 mL EtOAc
  3. extractionThe combined organics were back extracted 3×3 mL saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9842f0e564b849a09facc5b1cc1369b2
Source dataset
uspto-grants-2013_08
Patent number
US08519001B2

Reaction notes

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