Ethyl Acetate → HCID 42599128, compound

HRID 1898669Notes

Reaction equation

HRID 1898669 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([NH2:16])=[O:15])[CH2:6][CH2:5]2.CC[O:21]C(C)=O>C(C#N)(C)=O.O>[OH:21][C:7]([CH3:17])([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[CH3:18])[C:14]([NH2:16])=[O:15]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 53704167HCID 53704167, compound

Product 1

HCID 42599128HCID 42599128, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 694302-OxopropiononitrileSolvent

Procedure

A solution of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide (1.0 equiv.) in 3 mL AcCN (0.28 M) and a drop of water was cooled to 0° C. A solution of ceric ammonium nitrate (CAN) (2.2 equiv) in water (0.5 M) cooled to 0° C. was added dropwise over 2-3 minutes. The solution was then immediately treated with 10 mL EtOAc and the layers separated. The organic layer was washed 3×5 mL H2O and the combined aqueous phases back extracted with 3×5 mL EtOAc. The combined organics were washed with 10 mL saturated NaCl and dried over Na2SO4. Flash chromatography yielded the desired 2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide derivative.

Workup

  1. additionwas added dropwise over 2-3 minutes
  2. customthe layers separated
  3. washThe organic layer was washed 3×5 mL H2O
  4. extractionthe combined aqueous phases back extracted with 3×5 mL EtOAc
  5. washThe combined organics were washed with 10 mL saturated NaCl
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-8c524755777549b680bd237c005856f3
Source dataset
uspto-grants-2013_08
Patent number
US08519001B2

Reaction notes

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