Ethyl Acetate → HCID 25256726, compound

HRID 1898706Notes

Reaction equation

HRID 1898706 reaction equation
[OH:1][C:2]1[C:3]([CH3:21])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:20])([C:14]([NH:16][CH2:17][CH2:18][OH:19])=[O:15])[CH2:6][CH2:5]2.C(C#N)(C)=[O:23].O=[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+].CCOC(C)=O>O>[OH:23][C:7]([CH3:20])([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[CH3:21])[C:14]([NH:16][CH2:17][CH2:18][OH:19])=[O:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 694302-OxopropiononitrileHCID 180504Ceric ammonium nitrateHCID 67262915HCID 67262915, compound

Product 1

HCID 25256726HCID 25256726, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

6-Hydroxy-N-(2-hydroxyethyl)-2,5,7,8-tetramethylchroman-2-carboxamide (2.38 g, 8.11 mmol) was dissolved into 150 mL AcCN, cooled to 0° C. and treated with 9.75 g CAN (17.84 mmol) in 30 mL H2O over 20 minutes. EtOAc (150 mL) and H2O (20 mL) were then added, layers separated and the organic phase washed 21×20 mL H2O. The aqueous phase was back extracted 4×50 mL EtOAc and the combined organics washed with saturated NaCl, dried over Na2SO4 and concentrated to a yellow powder. Flash chromatography yielded 1.68 g of 2-hydroxy-N-(2-hydroxyethyl)-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid.

Workup

  1. customlayers separated
  2. washthe organic phase washed 21×20 mL H2O
  3. extractionThe aqueous phase was back extracted 4×50 mL EtOAc
  4. washthe combined organics washed with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a yellow powder

Sources & evidence

ORD record
ord-d18a3cda0fe94966839b1cd83c5c63a9
Source dataset
uspto-grants-2013_08
Patent number
US08519001B2

Reaction notes

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