Quinone → HCID 58288920, compound

HRID 1627958Notes

Reaction equation

HRID 1627958 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:16])[CH:14]=[CH2:15].C1(=O)C=CC(=O)C=C1>[N+]([O-])([O-])=O.[Ag+]>[C:10]([NH:9][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1/[CH:15]=[CH:14]/[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 4650QuinoneHCID 8846Butyl AcrylateHCID 11494Acetamide, N-(3-methoxyphenyl)-

Product 1

HCID 58288920HCID 58288920, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

N-(3-methoxy phenyl)acetamide (41 mg, 0.25 mmol), n-butyl acrylate (64 mg, 0.50 mmol), 1,4-benzoquinone (27 mg, 0.25 mmol), AgNO3 (85 mg, 0.5 mmol), and [Pd(MeCN)4](BF4)2 (11 mg, 0.025 mmol) were sequentially added under air to a reaction tube equipped with a stir bar and a septum. A degassed aqueous solution containing TPGS-M-PEG-750 (1.0 mL, 2 wt %) was added by syringe and the resulting mixture vigorously stirred for 20 h. After this time, the contents of the flask were quenched with aqueous NaHCO3 and extracted with EtOAc. The solution obtained was filtered through the plug of silica gel and anhydrous MgSO4, and then concentrated by rotary evaporation. The residue was purified by flash chromatography, eluting with 50% EtOAc/hexanes to afford the product as an off-white solid (60 mg, 83%).

Workup

  1. customequipped with a stir bar
  2. additionwas added by syringe
  3. customAfter this time, the contents of the flask were quenched with aqueous NaHCO3
  4. extractionextracted with EtOAc
  5. customThe solution obtained
  6. filtrationwas filtered through the plug of silica gel and anhydrous MgSO4
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by flash chromatography
  9. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-32c931b503fa47bbba2bc64f972eae40
Source dataset
uspto-grants-2014_07
Patent number
US08785665B2

Reaction notes

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